CH604500A5 - N-(Amino-sulphenyl)-N'-phenyl-formamidine derivs - Google Patents

N-(Amino-sulphenyl)-N'-phenyl-formamidine derivs

Info

Publication number: CH604500A5
Authority: CH; Switzerland
Prior art keywords: parts; methyl; phenyl; group; formula
Prior art date: 1975-01-16

Application number

CH53475A

Other languages

German (de)

English (en)

Inventor

Manfred Boeger

Jozef Dr Drabek

Original Assignee

Ciba Geigy 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.)

1975-01-16

Filing date

1975-01-16

Publication date

1978-09-15

1975-01-16 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1975-01-16 Priority to CH53475A priority Critical patent/CH604500A5/de

1976-01-07 Priority to NL7600124A priority patent/NL7600124A/xx

1976-01-12 Priority to FR7600561A priority patent/FR2297844A1/fr

1976-01-13 Priority to DE19762600987 priority patent/DE2600987A1/de

1976-01-14 Priority to CA243,548A priority patent/CA1080742A/fr

1976-01-15 Priority to BE163526A priority patent/BE837584A/fr

1976-01-15 Priority to ZA00760228A priority patent/ZA76228B/xx

1976-01-15 Priority to GB1606/76A priority patent/GB1529253A/en

1976-01-15 Priority to AT24576A priority patent/AT345615B/de

1976-01-15 Priority to IL48848A priority patent/IL48848A/xx

1976-01-16 Priority to JP393576A priority patent/JPS51125224A/ja

1976-01-16 Priority to SU762315752A priority patent/SU639412A3/ru

1977-05-02 Priority to US05/792,754 priority patent/US4115583A/en

1978-09-15 Publication of CH604500A5 publication Critical patent/CH604500A5/de

Links

CDLHETQLJOJBCE-UHFFFAOYSA-N N-aminosulfanyl-N'-phenylmethanimidamide Chemical compound NSNC=NC1=CC=CC=C1 CDLHETQLJOJBCE-UHFFFAOYSA-N 0.000 title abstract 2
-1 aminosulphenyl halides Chemical class 0.000 claims abstract description 8
150000001875 compounds Chemical class 0.000 claims description 26
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
229910052801 chlorine Inorganic materials 0.000 claims description 7
239000000460 chlorine Substances 0.000 claims description 7
125000004178 (C1-C4) alkyl group Chemical class 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
241000238631 Hexapoda Species 0.000 claims description 5
239000003795 chemical substances by application Substances 0.000 claims description 5
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
241000607479 Yersinia pestis Species 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
239000000575 pesticide Substances 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
YKSCOZXTXACAIX-UHFFFAOYSA-N n'-phenylmethanimidamide Chemical class N=CNC1=CC=CC=C1 YKSCOZXTXACAIX-UHFFFAOYSA-N 0.000 abstract 1
239000004480 active ingredient Substances 0.000 description 20
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
238000012360 testing method Methods 0.000 description 10
241000196324 Embryophyta Species 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000000126 substance Substances 0.000 description 9
239000000203 mixture Substances 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
239000008187 granular material Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
239000000839 emulsion Substances 0.000 description 6
239000005995 Aluminium silicate Substances 0.000 description 5
230000000895 acaricidal effect Effects 0.000 description 5
235000012211 aluminium silicate Nutrition 0.000 description 5
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 5
229920000151 polyglycol Polymers 0.000 description 5
239000010695 polyglycol Substances 0.000 description 5
239000007921 spray Substances 0.000 description 5
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 4
239000000654 additive Substances 0.000 description 4
239000000243 solution Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000008096 xylene Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
241001124076 Aphididae Species 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
241000721621 Myzus persicae Species 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000000969 carrier Substances 0.000 description 3
235000019993 champagne Nutrition 0.000 description 3
239000004495 emulsifiable concentrate Substances 0.000 description 3
238000000034 method Methods 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
241000238876 Acari Species 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
241000949016 Rhipicephalus bursa Species 0.000 description 2
241000238680 Rhipicephalus microplus Species 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
241001454293 Tetranychus urticae Species 0.000 description 2
240000006677 Vicia faba Species 0.000 description 2
235000010749 Vicia faba Nutrition 0.000 description 2
239000000642 acaricide Substances 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
239000002585 base Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
239000000428 dust Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
235000013601 eggs Nutrition 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
150000002191 fatty alcohols Chemical class 0.000 description 2
238000009472 formulation Methods 0.000 description 2
150000002431 hydrogen Chemical group 0.000 description 2
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
239000005457 ice water Substances 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
239000002917 insecticide Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
239000000843 powder Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
238000012545 processing Methods 0.000 description 2
235000015112 vegetable and seed oil Nutrition 0.000 description 2
239000008158 vegetable oil Substances 0.000 description 2
239000004563 wettable powder Substances 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
QQGRFMIMXPWKPM-UHFFFAOYSA-N 2,3,4-tributylphenol Chemical compound CCCCC1=CC=C(O)C(CCCC)=C1CCCC QQGRFMIMXPWKPM-UHFFFAOYSA-N 0.000 description 1
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical class CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 1
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical class CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
241000254032 Acrididae Species 0.000 description 1
241000238888 Argasidae Species 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
241000238660 Blattidae Species 0.000 description 1
241000907223 Bruchinae Species 0.000 description 1
241000257161 Calliphoridae Species 0.000 description 1
241001124134 Chrysomelidae Species 0.000 description 1
241001414835 Cimicidae Species 0.000 description 1
241000255749 Coccinellidae Species 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
241000256113 Culicidae Species 0.000 description 1
241000254171 Curculionidae Species 0.000 description 1
241001466044 Delphacidae Species 0.000 description 1
241000131287 Dermestidae Species 0.000 description 1
241001414830 Diaspididae Species 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
235000009161 Espostoa lanata Nutrition 0.000 description 1
240000001624 Espostoa lanata Species 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical compound NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 1
241000238816 Gryllidae Species 0.000 description 1
241001243087 Gryllotalpidae Species 0.000 description 1
241000238889 Ixodidae Species 0.000 description 1
241000257226 Muscidae Species 0.000 description 1
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
241000256259 Noctuidae Species 0.000 description 1
241000118205 Ovicides Species 0.000 description 1
244000046052 Phaseolus vulgaris Species 0.000 description 1
235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
241000258921 Pulicidae Species 0.000 description 1
241000255893 Pyralidae Species 0.000 description 1
241001124072 Reduviidae Species 0.000 description 1
241000254062 Scarabaeidae Species 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
241000254107 Tenebrionidae Species 0.000 description 1
241000255588 Tephritidae Species 0.000 description 1
241001454295 Tetranychidae Species 0.000 description 1
241000896028 Tettigoniidae Species 0.000 description 1
241000130767 Tineidae Species 0.000 description 1
241000131339 Tipulidae Species 0.000 description 1
235000002098 Vicia faba var. major Nutrition 0.000 description 1
GDVQUWOEJXJPNJ-UHFFFAOYSA-N [acetyl(methyl)amino] thiohypochlorite Chemical compound ClSN(C)C(C)=O GDVQUWOEJXJPNJ-UHFFFAOYSA-N 0.000 description 1
239000013543 active substance Substances 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
DNEHKUCSURWDGO-UHFFFAOYSA-N aluminum sodium Chemical compound [Na].[Al] DNEHKUCSURWDGO-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
229920005551 calcium lignosulfonate Polymers 0.000 description 1
OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 1
RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 1
150000004657 carbamic acid derivatives Chemical class 0.000 description 1
235000013877 carbamide Nutrition 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
150000003857 carboxamides Chemical class 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 description 1
238000007865 diluting Methods 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000013057 ectoparasiticide Substances 0.000 description 1
235000013399 edible fruits Nutrition 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
238000000227 grinding Methods 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
238000005470 impregnation Methods 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
230000000749 insecticidal effect Effects 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 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
230000001418 larval effect Effects 0.000 description 1
229920005610 lignin Polymers 0.000 description 1
230000007774 longterm Effects 0.000 description 1
238000002156 mixing Methods 0.000 description 1
MZCHBOYMVBQHQC-UHFFFAOYSA-N n-(4-chloro-2-methylphenyl)-n'-methylmethanimidamide Chemical compound CN=CNC1=CC=C(Cl)C=C1C MZCHBOYMVBQHQC-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
RBXVOQPAMPBADW-UHFFFAOYSA-N nitrous acid;phenol Chemical class ON=O.OC1=CC=CC=C1 RBXVOQPAMPBADW-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
150000003018 phosphorus compounds Chemical class 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000002002 slurry Substances 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 1
SRAWNDFHGTVUNZ-UHFFFAOYSA-M sodium;3,6-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC(CCCC)=CC2=CC(CCCC)=CC=C21 SRAWNDFHGTVUNZ-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 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 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/52—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing groups, e.g. carboxylic acid amidines
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/46—N-acyl derivatives
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/10—Sulfones; Sulfoxides
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48

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Life Sciences & Earth Sciences (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

CH53475A 1975-01-16 1975-01-16 N-(Amino-sulphenyl)-N'-phenyl-formamidine derivs CH604500A5 (en)

Priority Applications (13)

Application Number	Priority Date	Filing Date	Title
CH53475A CH604500A5 (en)	1975-01-16	1975-01-16	N-(Amino-sulphenyl)-N'-phenyl-formamidine derivs
NL7600124A NL7600124A (nl)	1975-01-16	1976-01-07	Werkwijze voor het bereiden van preparaten voor het bestrijden van schadelijke organismen.
FR7600561A FR2297844A1 (fr)	1975-01-16	1976-01-12	Nouvelles phenyl-formamidines sulfenylees utiles comme agents de lutte contre les parasites
DE19762600987 DE2600987A1 (de)	1975-01-16	1976-01-13	Schaedlingsbekaempfungsmittel
CA243,548A CA1080742A (fr)	1975-01-16	1976-01-14	Derives a effet pesticide de 1,3,5-triaza-4-sulfa-1-phenylhept-1-ene
BE163526A BE837584A (fr)	1975-01-16	1976-01-15	Nouvelles phenyl-formamidines sulfenylees utiles comme agents de lutte contre les parasites
ZA00760228A ZA76228B (en)	1975-01-16	1976-01-15	Pest control agents
GB1606/76A GB1529253A (en)	1975-01-16	1976-01-15	Phenylformamidines
AT24576A AT345615B (de)	1975-01-16	1976-01-15	Mittel zur bekaempfung von insekten und vertretern der ordnung akarina
IL48848A IL48848A (en)	1975-01-16	1976-01-15	N-sulphenylated phenylformamidines, their production and insecticidal and acaricidal compositions containing them
JP393576A JPS51125224A (en)	1975-01-16	1976-01-16	Phenylformamidine derivative* preparation thereof and combating agent* against harmuful organisms* containing same
SU762315752A SU639412A3 (ru)	1975-01-16	1976-01-16	Инсектицидноакарицидное средство
US05/792,754 US4115583A (en)	1975-01-16	1977-05-02	Pesticidal sulphenylated formamidine compounds

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH53475A CH604500A5 (en)	1975-01-16	1975-01-16	N-(Amino-sulphenyl)-N'-phenyl-formamidine derivs

Publications (1)

Publication Number	Publication Date
CH604500A5 true CH604500A5 (en)	1978-09-15

Family

ID=4189216

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH53475A CH604500A5 (en)	1975-01-16	1975-01-16	N-(Amino-sulphenyl)-N'-phenyl-formamidine derivs

Country Status (3)

Country	Link
BE (1)	BE837584A (fr)
CH (1)	CH604500A5 (fr)
ZA (1)	ZA76228B (fr)

1975
- 1975-01-16 CH CH53475A patent/CH604500A5/de not_active IP Right Cessation
1976
- 1976-01-15 ZA ZA00760228A patent/ZA76228B/xx unknown
- 1976-01-15 BE BE163526A patent/BE837584A/fr unknown

Also Published As

Publication number	Publication date
BE837584A (fr)	1976-07-15
ZA76228B (en)	1976-12-29

Legal Events

Date	Code	Title	Description
1983-09-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
EP0001203A1 (fr)	1979-04-04	N-phényl-N'-benzoyl-urées, procédé pour leur préparation, produits les contenant, et leur utilisation comme pesticides
CH592411A5 (en)	1977-10-31	Phenoxymethyl- and phenylthiomethyl-pyridine derivs - with insecticidal, acaricidal and plant-growth regulating activity
CH604500A5 (en)	1978-09-15	N-(Amino-sulphenyl)-N'-phenyl-formamidine derivs
DE2727614A1 (de)	1978-01-05	N,n'-bis-carbaminsaeure-sulfid-derivate, verfahren zu ihrer herstellung sowie schaedlingsbekaempfungsmittel
DE2751028C2 (de)	1986-08-28	Thiosubstituierte Carbamidsäure-Derivate, Verfahren zu ihrer Herstellung sowie Schädlingsbekämpfungsmittel
CH608692A5 (en)	1979-01-31	Pesticide comprising an N,N'-dicarbamic acid sulphide derivative as active ingredient
CH604522A5 (en)	1978-09-15	(4,5)-Benzospiro-(2,4)-heptane-(1)-carboxylate esters
CH627621A5 (en)	1982-01-29	Pesticide containing thio-substituted carbamic acid derivatives
DE2713651A1 (de)	1977-10-13	Spiro-(2,4)-hepta-1-carboxylate, verfahren zu ihrer herstellung und ihre verwendung
CH633681A5 (en)	1982-12-31	Pesticide containing thio-substituted carbamic acid derivatives
CH610181A5 (en)	1979-04-12	Pesticide comprising sulphenylated phenylformamidines as active ingredient
CH621922A5 (en)	1981-03-13	A pesticide
CH583517A5 (en)	1977-01-14	O,S-dialkyl-S-(oxadiazolyl-methyl)-dithiophosphates - used as pesticides, prepd. from chloro-methyl-oxadiazole and dithiophosphate salt
CH570764A5 (en)	1975-12-31	Phosphoramidothiolic acid esters - insecticides, acaricides, nematocides, viricides, bactericides, fungicides and herbicides
CH575717A5 (en)	1976-05-31	S-Arylthioalkyl-O,S-dialkyl dithiophosphates - with insecticidal, acaricidal, fungicidal, nematocidal activity, etc.
DE2430758A1 (de)	1975-01-23	Oxadiazolylverbindungen, verfahren zu ihrer herstellung und ihre verwendung zur schaedlingsbekaempfung
CH602010A5 (en)	1978-07-14	Alkynyloxy-benzyl-cyclopropane-carboxylates
CH583518A5 (en)	1977-01-14	0-(2-Alkenylphenyl) O,S-dialkyl thiophosphates - with insecticidal, acaricidal, fungicidal and nematocidal activity
CH576226A5 (en)	1976-06-15	Aralkyl phenyl ethers and thioethers - with acaricidal and insecticidal activity
DE2801072A1 (de)	1978-07-13	Carbamidosulfonylphenyl-formamidine, verfahren zu ihrer herstellung und ihre verwendung in der schaedlingsbekaempfung
CH583516A5 (en)	1977-01-14	O,S-dialkyl-S-(oxadiazolyl-methyl)-dithiophosphates - used as pesticides, prepd. from chloro-methyl-oxadiazole and dithiophosphate salt
CH602003A5 (en)	1978-07-14	Pesticidal compsn. esp. for control of insects and acarids
CH574713A5 (en)	1976-04-30	s-Picolyl phosphoridithioates - useful as insecticides, acaricides and plant-growth regulators
CH581434A5 (en)	1976-11-15	Cyanophenyl-thiolphosphates - insecticides and acaricides
CH556139A (de)	1974-11-29	Zur schaedlingsbekaempfung geeignetes mittel.