CH612421A5 - Pesticide comprising a (N-methyl- N'-phenylformamidino-mercapto)urea as active ingredient - Google Patents

Pesticide comprising a (N-methyl- N'-phenylformamidino-mercapto)urea as active ingredient

Info

Publication number: CH612421A5
Authority: CH; Switzerland
Prior art keywords: sep; radical; alkyl; atom; methyl
Prior art date: 1975-07-24

Application number

CH967475A

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.)

1975-07-24

Filing date

1975-07-24

Publication date

1979-07-31

1975-07-24 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1975-07-24 Priority to CH967475A priority Critical patent/CH612421A5/de

1976-07-08 Priority to SU762378585A priority patent/SU791197A3/ru

1976-07-20 Priority to FR7622120A priority patent/FR2318867A1/fr

1976-07-20 Priority to US05/707,149 priority patent/US4098902A/en

1976-07-21 Priority to DE19762632692 priority patent/DE2632692A1/de

1976-07-22 Priority to CA257,577A priority patent/CA1060035A/fr

1976-07-22 Priority to TR19146A priority patent/TR19146A/xx

1976-07-22 Priority to IL7650105A priority patent/IL50105A/xx

1976-07-22 Priority to AU16127/76A priority patent/AU505161B2/en

1976-07-23 Priority to BE169161A priority patent/BE844437A/fr

1976-07-23 Priority to NL7608219A priority patent/NL7608219A/xx

1976-07-23 Priority to AT545076A priority patent/AT350321B/de

1976-07-23 Priority to GB30873/76A priority patent/GB1538764A/en

1976-07-23 Priority to MX001795U priority patent/MX3484E/es

1976-07-23 Priority to BR7604811A priority patent/BR7604811A/pt

1976-07-23 Priority to ZA764429A priority patent/ZA764429B/xx

1976-07-24 Priority to JP51088614A priority patent/JPS5214729A/ja

1976-07-25 Priority to EG449/76A priority patent/EG12061A/xx

1979-07-31 Publication of CH612421A5 publication Critical patent/CH612421A5/de

Links

239000000575 pesticide Substances 0.000 title claims abstract description 5
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title claims description 3
239000004202 carbamide Substances 0.000 title claims description 3
239000004480 active ingredient Substances 0.000 title abstract description 21
150000001875 compounds Chemical class 0.000 claims abstract description 38
239000003795 chemical substances by application Substances 0.000 claims abstract description 14
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
239000001257 hydrogen Substances 0.000 claims abstract description 13
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 13
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 11
241000238631 Hexapoda Species 0.000 claims abstract description 9
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 5
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 5
125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims abstract description 4
229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
150000002431 hydrogen Chemical class 0.000 claims abstract 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 48
-1 C3-C8-cycloalkyl radical Chemical class 0.000 claims description 34
229910052801 chlorine Inorganic materials 0.000 claims description 23
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 18
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 17
239000000460 chlorine Substances 0.000 claims description 17
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 16
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 16
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 15
YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims description 13
125000001309 chloro group Chemical group Cl* 0.000 claims description 12
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 12
239000000203 mixture Substances 0.000 claims description 12
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
230000000694 effects Effects 0.000 claims description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
241000607479 Yersinia pestis Species 0.000 claims description 7
125000002757 morpholinyl group Chemical group 0.000 claims description 7
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
239000002585 base Substances 0.000 claims description 6
239000002904 solvent Substances 0.000 claims description 6
235000013877 carbamide Nutrition 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 5
238000000034 method Methods 0.000 claims description 5
239000008096 xylene Substances 0.000 claims description 5
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 claims description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 4
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
238000006243 chemical reaction Methods 0.000 claims description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
239000003085 diluting agent Substances 0.000 claims description 4
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical compound NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 claims description 3
XIPUIGPNIDKXJU-UHFFFAOYSA-N [CH]1CC1 Chemical group [CH]1CC1 XIPUIGPNIDKXJU-UHFFFAOYSA-N 0.000 claims description 3
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
125000004434 sulfur atom Chemical group 0.000 claims description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
150000003672 ureas Chemical class 0.000 claims description 3
VOLGAXAGEUPBDM-UHFFFAOYSA-N $l^{1}-oxidanylethane Chemical compound CC[O] VOLGAXAGEUPBDM-UHFFFAOYSA-N 0.000 claims description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 claims description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 2
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
239000003513 alkali Substances 0.000 claims description 2
229910052783 alkali metal Inorganic materials 0.000 claims description 2
150000001340 alkali metals Chemical class 0.000 claims description 2
150000001342 alkaline earth metals Chemical class 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
150000001408 amides Chemical class 0.000 claims description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
150000003857 carboxamides Chemical class 0.000 claims description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 claims description 2
POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 claims description 2
150000008282 halocarbons Chemical class 0.000 claims description 2
150000004679 hydroxides Chemical class 0.000 claims description 2
150000002576 ketones Chemical class 0.000 claims description 2
150000002825 nitriles Chemical class 0.000 claims description 2
230000000361 pesticidal effect Effects 0.000 claims description 2
239000011591 potassium Substances 0.000 claims description 2
229910052700 potassium Inorganic materials 0.000 claims description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
150000003254 radicals Chemical class 0.000 claims description 2
239000000376 reactant Substances 0.000 claims description 2
239000007858 starting material Substances 0.000 claims description 2
150000003512 tertiary amines Chemical class 0.000 claims description 2
125000004568 thiomorpholinyl group Chemical group 0.000 claims description 2
150000003738 xylenes Chemical class 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
229910052794 bromium Inorganic materials 0.000 claims 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
241000238876 Acari Species 0.000 abstract description 3
125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 3
229910052736 halogen Inorganic materials 0.000 abstract 1
150000002367 halogens Chemical class 0.000 abstract 1
238000012360 testing method Methods 0.000 description 17
239000000126 substance Substances 0.000 description 10
230000000895 acaricidal effect Effects 0.000 description 9
241000196324 Embryophyta Species 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
241001454293 Tetranychus urticae Species 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
239000008187 granular material Substances 0.000 description 6
239000005995 Aluminium silicate Substances 0.000 description 5
235000012211 aluminium silicate Nutrition 0.000 description 5
235000013601 eggs Nutrition 0.000 description 5
239000000839 emulsion Substances 0.000 description 5
238000002474 experimental method Methods 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
241000426497 Chilo suppressalis Species 0.000 description 4
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 4
239000000654 additive Substances 0.000 description 4
238000011156 evaluation Methods 0.000 description 4
239000000243 solution Substances 0.000 description 4
239000012085 test solution Substances 0.000 description 4
241001124076 Aphididae Species 0.000 description 3
241001425390 Aphis fabae Species 0.000 description 3
241001465754 Metazoa Species 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
240000007594 Oryza sativa Species 0.000 description 3
235000007164 Oryza sativa Nutrition 0.000 description 3
244000046052 Phaseolus vulgaris Species 0.000 description 3
239000000642 acaricide Substances 0.000 description 3
239000000969 carrier Substances 0.000 description 3
235000019993 champagne Nutrition 0.000 description 3
238000010790 dilution Methods 0.000 description 3
239000012895 dilution Substances 0.000 description 3
239000004495 emulsifiable concentrate Substances 0.000 description 3
230000002147 killing effect Effects 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
238000012545 processing Methods 0.000 description 3
235000009566 rice Nutrition 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
241000894007 species Species 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
241000949016 Rhipicephalus bursa Species 0.000 description 2
240000006677 Vicia faba Species 0.000 description 2
235000010749 Vicia faba Nutrition 0.000 description 2
239000013543 active substance Substances 0.000 description 2
239000000470 constituent Substances 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
230000006378 damage Effects 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
150000002191 fatty alcohols Chemical class 0.000 description 2
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
239000002917 insecticide Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
230000003151 ovacidal effect Effects 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
239000007787 solid Substances 0.000 description 2
239000007921 spray Substances 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 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
COSWCAGTKRUTQV-UHFFFAOYSA-N 1,1,3-trimethylurea Chemical compound CNC(=O)N(C)C COSWCAGTKRUTQV-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
241000254032 Acrididae Species 0.000 description 1
241000238888 Argasidae Species 0.000 description 1
241000238660 Blattidae 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
241001466044 Delphacidae Species 0.000 description 1
241001414830 Diaspididae Species 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
241000238816 Gryllidae Species 0.000 description 1
241001243087 Gryllotalpidae Species 0.000 description 1
241000238889 Ixodidae Species 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
241001124557 Lymantriidae Species 0.000 description 1
241001415279 Pseudococcidae Species 0.000 description 1
241000255893 Pyralidae Species 0.000 description 1
241001124072 Reduviidae Species 0.000 description 1
241001481703 Rhipicephalus <genus> Species 0.000 description 1
241000238680 Rhipicephalus microplus Species 0.000 description 1
241000255588 Tephritidae Species 0.000 description 1
241001454295 Tetranychidae Species 0.000 description 1
241000344246 Tetranychus cinnabarinus Species 0.000 description 1
241000896028 Tettigoniidae Species 0.000 description 1
241000131339 Tipulidae Species 0.000 description 1
235000002098 Vicia faba var. major Nutrition 0.000 description 1
YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 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
235000013339 cereals Nutrition 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000001816 cooling 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
YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
229940071161 dodecylbenzenesulfonate Drugs 0.000 description 1
239000000428 dust 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
238000005516 engineering process Methods 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
238000000227 grinding Methods 0.000 description 1
210000002837 heart atrium Anatomy 0.000 description 1
239000004009 herbicide Substances 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
230000001418 larval effect Effects 0.000 description 1
239000002267 larvicidal agent Substances 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
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
239000006072 paste Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
150000003018 phosphorus compounds Chemical class 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
230000008092 positive effect Effects 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
159000000000 sodium salts Chemical class 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
238000005507 spraying Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/215—Radicals derived from nitrogen analogues of carbonic acid
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
- C07C381/06—Compounds containing sulfur atoms only bound to two nitrogen atoms
- C07C381/08—Compounds containing sulfur atoms only bound to two nitrogen atoms having at least one of the nitrogen atoms acylated
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Dentistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Plant Pathology (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH967475A 1975-07-24 1975-07-24 Pesticide comprising a (N-methyl- N'-phenylformamidino-mercapto)urea as active ingredient CH612421A5 (en)

Priority Applications (18)

Application Number	Priority Date	Filing Date	Title
CH967475A CH612421A5 (en)	1975-07-24	1975-07-24	Pesticide comprising a (N-methyl- N'-phenylformamidino-mercapto)urea as active ingredient
SU762378585A SU791197A3 (ru)	1975-07-24	1976-07-08	Инсектоакарицидное средство
FR7622120A FR2318867A1 (fr)	1975-07-24	1976-07-20	Agents de lutte contre les parasites
US05/707,149 US4098902A (en)	1975-07-24	1976-07-20	1-phenyl-1,3,5,7-tetraaza-4-sulpha-hept-1-en-6-one derivatives
DE19762632692 DE2632692A1 (de)	1975-07-24	1976-07-21	Schaedlingsbekaempfungsmittel
CA257,577A CA1060035A (fr)	1975-07-24	1976-07-22	Insecticide
TR19146A TR19146A (tr)	1975-07-24	1976-07-22	Zararlilarla muecadele maddeleri
IL7650105A IL50105A (en)	1975-07-24	1976-07-22	1-phenyl-1,3,5,7-tetraaza-4-sulphahept-1-en-6-one derivatives their preparation and insecticidal of acaricidal compositions containing them
AU16127/76A AU505161B2 (en)	1975-07-24	1976-07-22	1, 3, 5, 7-tetraaza-4-sulpha-hept-1-en-6-one derivatives
BE169161A BE844437A (fr)	1975-07-24	1976-07-23	Agents de lutte contre les parasites
NL7608219A NL7608219A (nl)	1975-07-24	1976-07-23	Werkwijze voor het bereiden van preparaten voor het bestrijden van schadelijke organismen.
AT545076A AT350321B (de)	1975-07-24	1976-07-23	Insektizides oder akarizides mittel
GB30873/76A GB1538764A (en)	1975-07-24	1976-07-23	Tetraaza-sulpha-heptenone derivatives and their use as pesticides
MX001795U MX3484E (es)	1975-07-24	1976-07-23	Procedimiento para la preparacion de derivados de 1-fenil-1,3,5,7-tetraaza-4-sulfa-hept-1-en-6-ona
BR7604811A BR7604811A (pt)	1975-07-24	1976-07-23	Compostos organicos,processo para a preparacao destes,composicao para combater insetos daninhos e sua aplicacao
ZA764429A ZA764429B (en)	1975-07-24	1976-07-23	Pesticidal compositions
JP51088614A JPS5214729A (en)	1975-07-24	1976-07-24	11phenyll13577tetrazaa44sulfaaheptt11enee 66on delivative preparation thereof and combating agent* against harmful organisms* containing said coumpound
EG449/76A EG12061A (en)	1975-07-24	1976-07-25	Pesticidal compositions

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH967475A CH612421A5 (en)	1975-07-24	1975-07-24	Pesticide comprising a (N-methyl- N'-phenylformamidino-mercapto)urea as active ingredient

Publications (1)

Publication Number	Publication Date
CH612421A5 true CH612421A5 (en)	1979-07-31

Family

ID=4354451

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH967475A CH612421A5 (en)	1975-07-24	1975-07-24	Pesticide comprising a (N-methyl- N'-phenylformamidino-mercapto)urea as active ingredient

Country Status (3)

Country	Link
BE (1)	BE844437A (fr)
CH (1)	CH612421A5 (fr)
ZA (1)	ZA764429B (fr)

1975
- 1975-07-24 CH CH967475A patent/CH612421A5/de not_active IP Right Cessation
1976
- 1976-07-23 ZA ZA764429A patent/ZA764429B/xx unknown
- 1976-07-23 BE BE169161A patent/BE844437A/fr unknown

Also Published As

Publication number	Publication date
BE844437A (fr)	1977-01-24
ZA764429B (en)	1977-07-27

Legal Events

Date	Code	Title	Description
1983-03-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE2411809A1 (de)	1974-09-26	Thiolphosphorsaeureester, verfahren zu ihrer herstellung und ihre verwendung
DE3013908A1 (de)	1981-10-22	2-(n-aryl-, n-isoxazolylcarbonyl)-aminobutyrolactone, verfahren zu ihrer herstellung und diese enthaltende fungizide
AT328795B (de)	1976-04-12	Schadlingsbekampfungsmittel
CH580910A5 (fr)	1976-10-29
CH608692A5 (en)	1979-01-31	Pesticide comprising an N,N'-dicarbamic acid sulphide derivative as active ingredient
CH573206A5 (en)	1976-03-15	Pesticidal 5-halo-1,2,4-triazol-3-yl carbamates - e.g. 1-isopropyl-5-chloro-1,2,4-triazol-3-yl dimethylcarbamate
CH627621A5 (en)	1982-01-29	Pesticide containing thio-substituted carbamic acid derivatives
CH633681A5 (en)	1982-12-31	Pesticide containing thio-substituted carbamic acid derivatives
DE2430758A1 (de)	1975-01-23	Oxadiazolylverbindungen, verfahren zu ihrer herstellung und ihre verwendung zur schaedlingsbekaempfung
DE2439663A1 (de)	1975-03-06	Diphenylaetherphosphate, verfahren zu ihrer herstellung und ihre verwendung
CH574215A5 (en)	1976-04-15	0-(2-Alkenylphenyl) O,S-dialkyl thiophosphates - with insecticidal, acaricidal, fungicidal and nematocidal activity
DE2354586A1 (de)	1974-05-16	Neue ester
CH549942A (de)	1974-06-14	Schaedlingsbekaempfungsmittel.
CH571818A5 (en)	1976-01-30	O-Triazolyl O-alkyl (thio)phosph(on)ates - with biocidal (esp insecticidal and acaricidal)activity
CH570764A5 (en)	1975-12-31	Phosphoramidothiolic acid esters - insecticides, acaricides, nematocides, viricides, bactericides, fungicides and herbicides
CH621922A5 (en)	1981-03-13	A pesticide
CH571816A5 (en)	1976-01-30	O-Triazolyl O-alkyl (thio)phosph(on)ates - with biocidal (esp insecticidal) activity
CH583516A5 (en)	1977-01-14	O,S-dialkyl-S-(oxadiazolyl-methyl)-dithiophosphates - used as pesticides, prepd. from chloro-methyl-oxadiazole and dithiophosphate salt
CH575717A5 (en)	1976-05-31	S-Arylthioalkyl-O,S-dialkyl dithiophosphates - with insecticidal, acaricidal, fungicidal, nematocidal activity, etc.
CH571814A5 (en)	1976-01-30	3-(Thiophosphorylthiomethyl)-oxazolo (4,5-b) pyridine-2(3H)-(thi)ones - with biocidal (esp insecticidal and acaricidal) activity
CH590007A5 (en)	1977-07-29	1-(2-Cyanoethyl)-1,2,4-triazol-3-yl (thio)phosph(on)ates - prepd. by reacting 3-hydroxy cpds. with (thio)phosphor(on)yl halides
CH568013A5 (en)	1975-10-31	Trifluoromethyl nitrophenyl-thio-and dithio-phosphates - - insecticides, acaricides, fungicides and herbicides
CH583518A5 (en)	1977-01-14	0-(2-Alkenylphenyl) O,S-dialkyl thiophosphates - with insecticidal, acaricidal, fungicidal and nematocidal activity
CH571308A5 (en)	1976-01-15	Biocidal triazolyl dithio phosphates - prepd from dithio phosphoric acid halides and 3-hydroxy triazoles
CH620341A5 (en)	1980-11-28	Pesticides