IL28703A - 2,2,2-trichloroethylideneanilines - Google Patents

2,2,2-trichloroethylideneanilines

Info

Publication number: IL28703A
Authority: IL; Israel
Prior art keywords: aniline; formula; stands; process according; reaction
Prior art date: 1966-10-28

Application number

IL6728703A

Other languages

English (en)

Original Assignee

Bayer 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.)

1966-10-28

Filing date

1967-10-01

Publication date

1971-04-28

1967-10-01 Application filed by Bayer Ag filed Critical Bayer Ag

1971-04-28 Publication of IL28703A publication Critical patent/IL28703A/en

Links

BLCPBAGNBRMWLO-UHFFFAOYSA-N 2,2,2-trichloro-n-phenylethanimine Chemical class ClC(Cl)(Cl)C=NC1=CC=CC=C1 BLCPBAGNBRMWLO-UHFFFAOYSA-N 0.000 title claims description 5
150000001875 compounds Chemical class 0.000 claims description 26
238000000034 method Methods 0.000 claims description 21
HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 claims description 19
239000000203 mixture Substances 0.000 claims description 12
238000010992 reflux Methods 0.000 claims description 11
238000006243 chemical reaction Methods 0.000 claims description 10
239000003085 diluting agent Substances 0.000 claims description 10
FIOJWGRGPONADF-UHFFFAOYSA-N (sulfinylamino)benzene Chemical compound O=S=NC1=CC=CC=C1 FIOJWGRGPONADF-UHFFFAOYSA-N 0.000 claims description 9
230000000895 acaricidal effect Effects 0.000 claims description 8
239000002904 solvent Substances 0.000 claims description 8
239000007858 starting material Substances 0.000 claims description 8
239000007787 solid Substances 0.000 claims description 7
150000001448 anilines Chemical class 0.000 claims description 6
239000003054 catalyst Substances 0.000 claims description 6
239000000460 chlorine Substances 0.000 claims description 6
239000007788 liquid Substances 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
239000011541 reaction mixture Substances 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
239000004480 active ingredient Substances 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
239000004094 surface-active agent Substances 0.000 claims description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
239000002841 Lewis acid Substances 0.000 claims description 2
150000007517 lewis acids Chemical class 0.000 claims description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 48
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
239000005864 Sulphur Substances 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
239000004615 ingredient Substances 0.000 claims 1
-1 dioxan Chemical class 0.000 description 17
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 14
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
239000013078 crystal Substances 0.000 description 11
239000003921 oil Substances 0.000 description 10
238000002360 preparation method Methods 0.000 description 8
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
239000004291 sulphur dioxide Substances 0.000 description 7
235000010269 sulphur dioxide Nutrition 0.000 description 7
241000238876 Acari Species 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
241001454295 Tetranychidae Species 0.000 description 5
239000003995 emulsifying agent Substances 0.000 description 5
238000009472 formulation Methods 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
244000046052 Phaseolus vulgaris Species 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000000969 carrier Substances 0.000 description 3
XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
QQTGIDAYGJBWBK-UHFFFAOYSA-N 3-aminobenzenesulfinyl chloride Chemical compound ClS(=O)C=1C=C(N)C=CC=1 QQTGIDAYGJBWBK-UHFFFAOYSA-N 0.000 description 2
NOVZROKPTJWPCM-UHFFFAOYSA-N 4-aminobenzene-1,2,3,5-tetrasulfinyl chloride Chemical compound ClS(=O)C1=C(N)C(=CC(=C1S(=O)Cl)S(=O)Cl)S(=O)Cl NOVZROKPTJWPCM-UHFFFAOYSA-N 0.000 description 2
CKAKPFDSVJHPLS-UHFFFAOYSA-N 4-aminobenzene-1,3-disulfinyl chloride Chemical compound ClS(=O)C1=C(N)C=CC(=C1)S(=O)Cl CKAKPFDSVJHPLS-UHFFFAOYSA-N 0.000 description 2
VILINLJKLIWZKQ-UHFFFAOYSA-N 5-aminobenzene-1,3-disulfinyl chloride Chemical compound ClS(=O)C=1C=C(N)C=C(C1)S(=O)Cl VILINLJKLIWZKQ-UHFFFAOYSA-N 0.000 description 2
239000004606 Fillers/Extenders Substances 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
241001454293 Tetranychus urticae Species 0.000 description 2
125000002877 alkyl aryl group Chemical group 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
238000004821 distillation Methods 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
239000008187 granular material Substances 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
239000011707 mineral Substances 0.000 description 2
239000006072 paste Substances 0.000 description 2
229920000151 polyglycol Polymers 0.000 description 2
239000010695 polyglycol Substances 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000000243 solution Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
239000008096 xylene Substances 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
XVNXSKZEAASNNY-UHFFFAOYSA-N 2,2,2-trichloro-N-(2,4-dichlorophenyl)ethanimine Chemical compound ClC(C=NC1=C(C=C(C=C1)Cl)Cl)(Cl)Cl XVNXSKZEAASNNY-UHFFFAOYSA-N 0.000 description 1
LXCLPHJRGDTDDB-UHFFFAOYSA-N 2,3,4,6-tetrachloroaniline Chemical compound NC1=C(Cl)C=C(Cl)C(Cl)=C1Cl LXCLPHJRGDTDDB-UHFFFAOYSA-N 0.000 description 1
KQCMTOWTPBNWDB-UHFFFAOYSA-N 2,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C=C1Cl KQCMTOWTPBNWDB-UHFFFAOYSA-N 0.000 description 1
LEFBVSWOPDWLLW-UHFFFAOYSA-N 2-amino-5-methylbenzenesulfinyl chloride Chemical compound CC1=CC(=C(N)C=C1)S(=O)Cl LEFBVSWOPDWLLW-UHFFFAOYSA-N 0.000 description 1
LBCMTOAWWCSXRX-UHFFFAOYSA-N 2-aminobenzene-1,3,5-trisulfinyl bromide Chemical compound BrS(=O)C1=C(N)C(=CC(=C1)S(=O)Br)S(=O)Br LBCMTOAWWCSXRX-UHFFFAOYSA-N 0.000 description 1
NMAOJDZIBCTUGU-UHFFFAOYSA-N 2-aminobenzenesulfinyl chloride Chemical compound NC1=CC=CC=C1S(Cl)=O NMAOJDZIBCTUGU-UHFFFAOYSA-N 0.000 description 1
AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
ICLPJYNBMUNHBG-UHFFFAOYSA-N 3-amino-4-methylbenzenesulfinyl bromide Chemical compound CC1=C(N)C=C(C=C1)S(=O)Br ICLPJYNBMUNHBG-UHFFFAOYSA-N 0.000 description 1
PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 1
KLCOBXYYLYDJRP-UHFFFAOYSA-N 4-amino-3,5-dibromobenzenesulfinyl chloride Chemical compound BrC1=C(N)C(=CC(=C1)S(=O)Cl)Br KLCOBXYYLYDJRP-UHFFFAOYSA-N 0.000 description 1
CHFMNICNTXYBIB-UHFFFAOYSA-N 4-aminobenzenesulfinyl bromide Chemical compound BrS(=O)C1=CC=C(N)C=C1 CHFMNICNTXYBIB-UHFFFAOYSA-N 0.000 description 1
PIXZEBNRTHRVEN-UHFFFAOYSA-N 4-aminobenzenesulfinyl chloride Chemical compound ClS(=O)C1=CC=C(N)C=C1 PIXZEBNRTHRVEN-UHFFFAOYSA-N 0.000 description 1
CZJPOTJTFKYOAW-UHFFFAOYSA-N 4-chloro-2-methylsulfinylaniline Chemical compound CS(=O)C1=CC(Cl)=CC=C1N CZJPOTJTFKYOAW-UHFFFAOYSA-N 0.000 description 1
YTSWZAYOZFBVMZ-UHFFFAOYSA-N 6-aminobenzene-1,2,3,4,5-pentasulfinyl chloride Chemical compound ClS(=O)C1=C(C(=C(C(=C1N)S(=O)Cl)S(=O)Cl)S(=O)Cl)S(=O)Cl YTSWZAYOZFBVMZ-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
241000239290 Araneae Species 0.000 description 1
229910015900 BF3 Inorganic materials 0.000 description 1
DWFJIHYACQAYIP-UHFFFAOYSA-N BrC1=C(N)C(=CC(=C1)Br)S(=O)C Chemical compound BrC1=C(N)C(=CC(=C1)Br)S(=O)C DWFJIHYACQAYIP-UHFFFAOYSA-N 0.000 description 1
PKQDONZKLARBCZ-UHFFFAOYSA-N CC1=C(N)C(=CC(=C1)C)S(=O)Br Chemical compound CC1=C(N)C(=CC(=C1)C)S(=O)Br PKQDONZKLARBCZ-UHFFFAOYSA-N 0.000 description 1
PWPIPRTZHMBHQC-UHFFFAOYSA-N CC1=C(N)C(=CC=C1)S(=O)Cl Chemical compound CC1=C(N)C(=CC=C1)S(=O)Cl PWPIPRTZHMBHQC-UHFFFAOYSA-N 0.000 description 1
GINCAKKCSBOHML-UHFFFAOYSA-N ClC1=C(N)C=C(C=C1)S(=O)C(F)(F)F Chemical compound ClC1=C(N)C=C(C=C1)S(=O)C(F)(F)F GINCAKKCSBOHML-UHFFFAOYSA-N 0.000 description 1
OEPQEYLFLLLKLY-UHFFFAOYSA-N ClS(=O)C1=C(N)C=C(C(=C1S(=O)Cl)S(=O)Cl)S(=O)Cl Chemical compound ClS(=O)C1=C(N)C=C(C(=C1S(=O)Cl)S(=O)Cl)S(=O)Cl OEPQEYLFLLLKLY-UHFFFAOYSA-N 0.000 description 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
GYIGPCNNDCTELC-UHFFFAOYSA-N NC1=CC(C(F)(F)F)=CC=C1S(Cl)=O Chemical compound NC1=CC(C(F)(F)F)=CC=C1S(Cl)=O GYIGPCNNDCTELC-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
241000488583 Panonychus ulmi Species 0.000 description 1
235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
241001396980 Phytonemus pallidus Species 0.000 description 1
231100000674 Phytotoxicity Toxicity 0.000 description 1
235000001537 Ribes X gardonianum Nutrition 0.000 description 1
235000001535 Ribes X utile Nutrition 0.000 description 1
235000016919 Ribes petraeum Nutrition 0.000 description 1
244000281247 Ribes rubrum Species 0.000 description 1
235000002355 Ribes spicatum Nutrition 0.000 description 1
241001454294 Tetranychus Species 0.000 description 1
229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
239000000642 acaricide Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
150000008422 chlorobenzenes Chemical class 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
230000006378 damage Effects 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
229960001760 dimethyl sulfoxide Drugs 0.000 description 1
238000010410 dusting Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229920005610 lignin Polymers 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
229940043265 methyl isobutyl ketone Drugs 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
150000003014 phosphoric acid esters Chemical class 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
238000005507 spraying Methods 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
239000002699 waste material Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

IL6728703A 1966-10-28 1967-10-01 2,2,2-trichloroethylideneanilines IL28703A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DEF0050561		1966-10-28

Publications (1)

Publication Number	Publication Date
IL28703A true IL28703A (en)	1971-04-28

Family

ID=7103891

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL6728703A IL28703A (en)	1966-10-28	1967-10-01	2,2,2-trichloroethylideneanilines

Country Status (8)

Country	Link
US (1)	US3558705A (de)
BE (1)	BE705685A (de)
CH (1)	CH487851A (de)
DE (1)	DE1568612A1 (de)
ES (1)	ES346448A1 (de)
GB (1)	GB1149138A (de)
IL (1)	IL28703A (de)
NL (1)	NL6713958A (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3521424C1 (de) *	1985-06-14	1986-06-12	M.A.N.- Roland Druckmaschinen AG, 6050 Offenbach	Farbwalze fuer Druckmaschinen

1966
- 1966-10-28 DE DE19661568612 patent/DE1568612A1/de active Pending
1967
- 1967-09-27 CH CH1347867A patent/CH487851A/de not_active IP Right Cessation
- 1967-10-01 IL IL6728703A patent/IL28703A/en unknown
- 1967-10-05 GB GB45486/67A patent/GB1149138A/en not_active Expired
- 1967-10-13 NL NL6713958A patent/NL6713958A/xx unknown
- 1967-10-25 US US677878A patent/US3558705A/en not_active Expired - Lifetime
- 1967-10-26 BE BE705685D patent/BE705685A/xx unknown
- 1967-10-26 ES ES346448A patent/ES346448A1/es not_active Expired

Also Published As

Publication number	Publication date
US3558705A (en)	1971-01-26
DE1568612A1 (de)	1970-04-02
GB1149138A (en)	1969-04-16
ES346448A1 (es)	1968-12-16
BE705685A (de)	1968-04-26
CH487851A (de)	1970-03-31
NL6713958A (de)	1968-04-29

Publication	Publication Date	Title
EP0436680B1 (de)	1994-09-07	Heterocyclische verbindungen
US3227758A (en)	1966-01-04	Phenalkylamines
US2384811A (en)	1945-09-18	Insecticidal amides
IL28703A (en)	1971-04-28	2,2,2-trichloroethylideneanilines
US3522293A (en)	1970-07-28	Selected 3-(trifluoromethylthio)propionyl compounds
US2854325A (en)	1958-09-30	Herbicidal process and composition
IL26698A (en)	1970-03-22	Amidothionophosphoric acid ester
US3224861A (en)	1965-12-21	Controlling undesired vegetation with benzyl hexamethyleniminecarbothioates
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EP0157270B1 (de)	1988-06-15	Verfahren zur Herstellung von tetrachlorierten Benzo-1,4-dioxenen
US3394397A (en)	1968-07-23	Nu-4-bromo-2-methylphenyl-nu', nu'-dimethylformamidine and process for preparing thesame
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US3932408A (en)	1976-01-13	Pyrimidines and process of making the same
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US2872477A (en)	1959-02-03	alpha-(dialkylamino)-6-phenyl-o-cresol esters
US3210177A (en)	1965-10-05	Herbicidal method
US3435072A (en)	1969-03-25	Cyclohexeneimine thiocyanates