CH526587A - Verfahren zur Herstellung neuer Thiophosphorsäureamidester - Google Patents

Verfahren zur Herstellung neuer Thiophosphorsäureamidester

Info

Publication number: CH526587A
Authority: CH; Switzerland
Prior art keywords: sep; general formula; hydrogen; compound; acid acceptor
Prior art date: 1969-07-18

Application number

CH1564371A

Other languages

German (de)

English (en)

Inventor

Leber Jean-Pierre

Lutz Karl

Original Assignee

Sandoz Ag

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.)

1969-07-18

Filing date

1969-07-18

Publication date

1972-08-15

1969-07-18 Application filed by Sandoz Ag filed Critical Sandoz Ag

1969-07-18 Priority to CH1564371A priority Critical patent/CH526587A/de

1972-08-15 Publication of CH526587A publication Critical patent/CH526587A/de

Links

-1 thio phosphoric acid imide esters Chemical class 0.000 title claims abstract description 11
230000002141 anti-parasite Effects 0.000 title abstract 2
239000003096 antiparasitic agent Substances 0.000 title abstract 2
239000002253 acid Substances 0.000 claims abstract description 16
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
238000006243 chemical reaction Methods 0.000 claims abstract description 9
125000000217 alkyl group Chemical group 0.000 claims abstract description 6
125000005843 halogen group Chemical group 0.000 claims abstract description 6
229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
229910052794 bromium Inorganic materials 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 32
238000000034 method Methods 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
241000244206 Nematoda Species 0.000 claims description 7
239000000460 chlorine Chemical group 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
241000238631 Hexapoda Species 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
229910052783 alkali metal Chemical group 0.000 claims description 3
150000001340 alkali metals Chemical group 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 3
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims 1
230000001419 dependent effect Effects 0.000 claims 1
230000001069 nematicidal effect Effects 0.000 abstract description 5
230000000895 acaricidal effect Effects 0.000 abstract description 3
239000005645 nematicide Substances 0.000 abstract description 2
239000000642 acaricide Substances 0.000 abstract 1
229910052736 halogen Inorganic materials 0.000 abstract 1
239000002917 insecticide Substances 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
239000004480 active ingredient Substances 0.000 description 14
239000000203 mixture Substances 0.000 description 13
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
230000006378 damage Effects 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
230000000694 effects Effects 0.000 description 9
239000003208 petroleum Substances 0.000 description 9
241001465754 Metazoa Species 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
239000007921 spray Substances 0.000 description 6
238000011156 evaluation Methods 0.000 description 5
230000000749 insecticidal effect Effects 0.000 description 5
239000000243 solution Substances 0.000 description 5
241001425390 Aphis fabae Species 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
239000000839 emulsion Substances 0.000 description 4
239000000575 pesticide Substances 0.000 description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
241001388466 Bruchus rufimanus Species 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
240000006677 Vicia faba Species 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
238000009472 formulation Methods 0.000 description 3
239000011521 glass Substances 0.000 description 3
150000008282 halocarbons Chemical class 0.000 description 3
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
WQYSXVGEZYESBR-UHFFFAOYSA-N thiophosphoryl chloride Chemical compound ClP(Cl)(Cl)=S WQYSXVGEZYESBR-UHFFFAOYSA-N 0.000 description 3
239000008096 xylene Substances 0.000 description 3
241000238876 Acari Species 0.000 description 2
241001124076 Aphididae Species 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
229910001369 Brass Inorganic materials 0.000 description 2
241000254001 Carausius Species 0.000 description 2
241000122098 Ephestia kuehniella Species 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 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
241000244199 Panagrellus redivivus Species 0.000 description 2
241000253999 Phasmatodea Species 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
241000607479 Yersinia pestis Species 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000010951 brass Substances 0.000 description 2
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000003921 oil Substances 0.000 description 2
238000005191 phase separation Methods 0.000 description 2
229910052698 phosphorus Inorganic materials 0.000 description 2
238000000926 separation method Methods 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
238000003756 stirring Methods 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
241001143309 Acanthoscelides obtectus Species 0.000 description 1
241000907225 Bruchidius Species 0.000 description 1
241000254000 Carausius morosus Species 0.000 description 1
241001107116 Castanospermum australe Species 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 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 description 1
229910018894 PSCl3 Inorganic materials 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
241001454295 Tetranychidae Species 0.000 description 1
241000233835 Tradescantia Species 0.000 description 1
235000010749 Vicia faba Nutrition 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000000440 bentonite Substances 0.000 description 1
229910000278 bentonite Inorganic materials 0.000 description 1
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
235000021279 black bean Nutrition 0.000 description 1
238000009835 boiling Methods 0.000 description 1
235000010633 broth Nutrition 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical group C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000428 dust Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000000605 extraction Methods 0.000 description 1
230000003031 feeding effect Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
229920000151 polyglycol Polymers 0.000 description 1
239000010695 polyglycol Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
GVIIRWAJDFKJMJ-UHFFFAOYSA-N propan-2-yl 3-oxobutanoate Chemical compound CC(C)OC(=O)CC(C)=O GVIIRWAJDFKJMJ-UHFFFAOYSA-N 0.000 description 1
239000008262 pumice Substances 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000004575 stone Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
KLBOFRLEHJAXIU-UHFFFAOYSA-N tributylazanium;chloride Chemical compound Cl.CCCCN(CCCC)CCCC KLBOFRLEHJAXIU-UHFFFAOYSA-N 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/20—Esters of thiophosphoric acids containing P-halide groups
- 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
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2404—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2412—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic of unsaturated acyclic alcohols
- 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
- C07F9/22—Amides of acids of phosphorus
- C07F9/26—Amides of acids of phosphorus containing P-halide groups

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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

CH1564371A 1969-07-18 1969-07-18 Verfahren zur Herstellung neuer Thiophosphorsäureamidester CH526587A (de)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CH1564371A CH526587A (de)	1969-07-18	1969-07-18	Verfahren zur Herstellung neuer Thiophosphorsäureamidester

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH1564371A CH526587A (de)	1969-07-18	1969-07-18	Verfahren zur Herstellung neuer Thiophosphorsäureamidester
CH1102869A CH526585A (de)	1969-07-18	1969-07-18	Verfahren zur Herstellung neuer Thiophosphorsäureamidester

Publications (1)

Publication Number	Publication Date
CH526587A true CH526587A (de)	1972-08-15

Family

ID=4369307

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
CH1564371A CH526587A (de)	1969-07-18	1969-07-18	Verfahren zur Herstellung neuer Thiophosphorsäureamidester
CH1102869A CH526585A (de)	1969-07-18	1969-07-18	Verfahren zur Herstellung neuer Thiophosphorsäureamidester
CH1564271A CH526586A (de)	1969-07-18	1969-07-18	Verfahren zur Herstellung neuer Thiophosphorsäureamidester

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
CH1102869A CH526585A (de)	1969-07-18	1969-07-18	Verfahren zur Herstellung neuer Thiophosphorsäureamidester
CH1564271A CH526586A (de)	1969-07-18	1969-07-18	Verfahren zur Herstellung neuer Thiophosphorsäureamidester

Country Status (8)

Country	Link
JP (1)	JPS57131707A (cs)
AT (1)	AT315199B (cs)
CH (3)	CH526587A (cs)
CS (1)	CS199225B2 (cs)
PL (1)	PL81290B1 (cs)
SU (3)	SU497779A3 (cs)
TR (1)	TR17496A (cs)
ZA (1)	ZA704936B (cs)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8514853D0 (en) *	1985-06-12	1985-07-17	Sandoz Ltd	Controlling termites
JPH073627U (ja) *	1992-07-07	1995-01-20	幸雄中濱	医療ベッド用電動昇降機

1969
- 1969-07-18 CH CH1564371A patent/CH526587A/de not_active IP Right Cessation
- 1969-07-18 CH CH1102869A patent/CH526585A/de not_active IP Right Cessation
- 1969-07-18 CH CH1564271A patent/CH526586A/de not_active IP Right Cessation
1970
- 1970-07-16 CS CS705023A patent/CS199225B2/cs unknown
- 1970-07-16 SU SU1703109A patent/SU497779A3/ru active
- 1970-07-16 TR TR17496A patent/TR17496A/xx unknown
- 1970-07-16 SU SU1467354A patent/SU434637A3/ru active
- 1970-07-16 PL PL1970142106A patent/PL81290B1/pl unknown
- 1970-07-17 ZA ZA704936A patent/ZA704936B/xx unknown
- 1970-07-17 AT AT654170A patent/AT315199B/de not_active IP Right Cessation
1971
- 1971-10-04 SU SU1703106A patent/SU539531A3/ru active
1979
- 1979-09-17 JP JP54119986A patent/JPS57131707A/ja active Pending

Also Published As

Publication number	Publication date
CH526586A (de)	1972-08-15
SU539531A3 (ru)	1976-12-15
SU434637A3 (ru)	1974-06-30
ZA704936B (en)	1972-02-23
SU497779A3 (ru)	1975-12-30
JPS57131707A (en)	1982-08-14
PL81290B1 (cs)	1975-08-30
AT315199B (de)	1974-05-10
CS199225B2 (en)	1980-07-31
TR17496A (tr)	1975-07-23
CH526585A (de)	1972-08-15

Legal Events

Date	Code	Title	Description
1978-02-28	PL	Patent ceased

Publication	Publication Date	Title
DE1493646A1 (de)	1969-11-06	Verfahren zur Herstellung von Cumarany-N-methylcarbaminsaeureestern
DE1545817B1 (de)	1971-04-22	Phosphor-,Phosphon-,Thionophosphor- und Thionophosphonsaeureester des 2-Hydroxychinoxalins
CH526587A (de)	1972-08-15	Verfahren zur Herstellung neuer Thiophosphorsäureamidester
DE1643608B2 (de)	1973-09-13	Cyclobutenphosphorsaureester, Ver fahren zu ihrer Herstellung und Schad lingsbekampfungsmittel
DE2139246A1 (de)	1972-02-17	Verfahren zur Herstellung neuer Phosphorsaureamidester
DE1916268A1 (de)	1969-10-23	Schaedlingsbekaempfungsmittel
DE2037508A1 (de)	1971-02-18	Verfahren zur Herstellung neuer Phosphorsaureamidester
DE2030509A1 (de)	1971-12-30	2-Cyanovinyl-(thio)-phosphor- bzw. -phosphonsäure-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide
DE1545813A1 (de)	1969-10-16	Verfahren zur Herstellung von Thiol- bzw. Thionothiolphosphor-(-phosphon)saeureestern
DE2035103C3 (de)	1976-02-05	Neue Thiophosphorsäureamidester, deren Herstellung, sowie diese enthaltende insektizide, akarizide und nematozide Mittel
DE2002892A1 (de)	1970-07-30	Verfahren zur Herstellung von 0,0-Dimethyl-thionophosphorsaeure-[0-chinoxalyl-(2)]-ester
DE1545817C (de)	1971-12-09	Phosphor , Phosphon , Thionophosphor und Thionophosphonsaureester des 2 Hydroxy chinoxaline
CH520165A (de)	1972-03-15	Verfahren zur Herstellung neuer Phosphorsäureamidester
AT336341B (de)	1977-04-25	Schadlingsbekampfungsmittel
DE1062239B (de)	1959-07-30	Verfahren zur Herstellung von Thiophosphorsaeureestern
CH523285A (de)	1972-05-31	Verfahren zur Herstellung neuer Phosphorsäureamidester
DE2163063A1 (de)	1973-06-20	Dialkylthionophosphorsaeureester
DE2035001A1 (de)	1971-01-28	Verfahren zur Herstellung neuer Thiophosphorsäureester
DE3302095A1 (de)	1984-07-26	O,s-dialkyl-s- (carbamoyloxyalkyl) -dithiophosphorsaeureester, verfahren zu ihrer herstellung sowie ihre verwendung als schaedlingsbekaempfungsmittel
DE1934459A1 (de)	1970-01-15	Verfahren zur Herstellung neuer Phosphorsaeureester
AT273581B (de)	1969-08-25	Insektizides und akarizides Mittel sowie Verfahren zu dessen Herstellung
CH544037A (de)	1973-11-15	Verfahren zur Herstellung neuer 1.2.3-Trithianverbindungen
DE2243612A1 (de)	1973-03-15	Thiophen-glyoxylonitril-oxim-phosphorsaeurederivate und ihre verwendung
CH554376A (de)	1974-09-30	Verfahren zur herstellung neuer phosphorsaeureamidester.
DE3205456A1 (de)	1983-08-25	Halogenierte 1-hydroxipyrazole und verfahren zu ihrer herstellung