IL35153A - N-phenylcarboxylic acid amidines,their preparation and their use as acaricides - Google Patents

N-phenylcarboxylic acid amidines,their preparation and their use as acaricides

Info

Publication number: IL35153A
Authority: IL; Israel
Prior art keywords: compound; formula; methyl; ethyl; process according
Prior art date: 1969-09-25

Application number

IL35153A

Other languages

English (en)

Other versions

IL35153A0 (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.)

1969-09-25

Filing date

1970-08-24

Publication date

1974-09-10

1970-08-24 Application filed by Bayer Ag filed Critical Bayer Ag

1970-10-30 Publication of IL35153A0 publication Critical patent/IL35153A0/xx

1974-09-10 Publication of IL35153A publication Critical patent/IL35153A/en

Links

230000000895 acaricidal effect Effects 0.000 title claims description 4
238000002360 preparation method Methods 0.000 title description 4
239000000642 acaricide Substances 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 50
238000000034 method Methods 0.000 claims description 21
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
239000000203 mixture Substances 0.000 claims description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
241001465754 Metazoa Species 0.000 claims description 8
239000003795 chemical substances by application Substances 0.000 claims description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
-1 inorganic acid halide Chemical class 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 6
244000078703 ectoparasite Species 0.000 claims description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
241000607479 Yersinia pestis Species 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 4
150000001409 amidines Chemical class 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 4
239000003085 diluting agent Substances 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
239000007787 solid Substances 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
239000007788 liquid Substances 0.000 claims description 3
239000004480 active ingredient Substances 0.000 claims description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
239000012442 inert solvent Substances 0.000 claims description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 2
125000004429 atom Chemical group 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 claims 1
239000004094 surface-active agent Substances 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
241000238876 Acari Species 0.000 description 7
235000013601 eggs Nutrition 0.000 description 6
230000003151 ovacidal effect Effects 0.000 description 6
239000000243 solution Substances 0.000 description 5
241001481703 Rhipicephalus <genus> Species 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
238000010992 reflux Methods 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
241000238680 Rhipicephalus microplus Species 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
238000000151 deposition Methods 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
239000011591 potassium Substances 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
239000007858 starting material Substances 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
241001494479 Pecora Species 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
238000009835 boiling Methods 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000009472 formulation Methods 0.000 description 2
239000005457 ice water Substances 0.000 description 2
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
239000010695 polyglycol Substances 0.000 description 2
229920000151 polyglycol Polymers 0.000 description 2
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 2
235000019260 propionic acid Nutrition 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
QFUSOYKIDBRREL-NSCUHMNNSA-N (e)-but-2-en-1-amine Chemical compound C\C=C\CN QFUSOYKIDBRREL-NSCUHMNNSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
241000283690 Bos taurus Species 0.000 description 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-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
241000771994 Melophagus ovinus Species 0.000 description 1
241000403354 Microplus Species 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
241000620638 Psoroptes cuniculi Species 0.000 description 1
102400000830 Saposin-B Human genes 0.000 description 1
101800001697 Saposin-B Proteins 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
AVMNFQHJOOYCAP-UHFFFAOYSA-N acetic acid;propanoic acid Chemical compound CC(O)=O.CCC(O)=O AVMNFQHJOOYCAP-UHFFFAOYSA-N 0.000 description 1
YBCVMFKXIKNREZ-UHFFFAOYSA-N acoh acetic acid Chemical compound CC(O)=O.CC(O)=O YBCVMFKXIKNREZ-UHFFFAOYSA-N 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
150000001448 anilines Chemical class 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
MWOBKFYERIDQSZ-UHFFFAOYSA-N benzene;sodium Chemical compound [Na].C1=CC=CC=C1 MWOBKFYERIDQSZ-UHFFFAOYSA-N 0.000 description 1
ORSVWFJAARXBHC-UHFFFAOYSA-N carbamic acid;phosphoric acid Chemical class NC(O)=O.OP(O)(O)=O ORSVWFJAARXBHC-UHFFFAOYSA-N 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
229940125797 compound 12 Drugs 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
230000008021 deposition Effects 0.000 description 1
150000004816 dichlorobenzenes Chemical class 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
238000007654 immersion Methods 0.000 description 1
229910001502 inorganic halide Inorganic materials 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
230000002147 killing effect Effects 0.000 description 1
244000144972 livestock Species 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
239000011707 mineral Substances 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
231100000194 ovacidal Toxicity 0.000 description 1
230000003071 parasitic effect Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
150000003014 phosphoric acid esters Chemical class 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
244000144977 poultry Species 0.000 description 1
239000000843 powder Substances 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000005049 silicon tetrachloride Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
241000894007 species Species 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
125000005031 thiocyano group Chemical group S(C#N)* 0.000 description 1
239000002699 waste material Substances 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
- A47—FURNITURE; DOMESTIC ARTICLES OR APPLIANCES; COFFEE MILLS; SPICE MILLS; SUCTION CLEANERS IN GENERAL
- A47J—KITCHEN EQUIPMENT; COFFEE MILLS; SPICE MILLS; APPARATUS FOR MAKING BEVERAGES
- A47J31/00—Apparatus for making beverages
- A47J31/40—Beverage-making apparatus with dispensing means for adding a measured quantity of ingredients, e.g. coffee, water, sugar, cocoa, milk, tea

Landscapes

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

IL35153A 1969-09-25 1970-08-24 N-phenylcarboxylic acid amidines,their preparation and their use as acaricides IL35153A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE1948459A DE1948459B2 (de)	1969-09-25	1969-09-25	N-Phenylcarbonsäureamidine, Verfahren zu ihrer Herstellung und akarizide Mittel

Publications (2)

Publication Number	Publication Date
IL35153A0 IL35153A0 (en)	1970-10-30
IL35153A true IL35153A (en)	1974-09-10

Family

ID=5746452

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL35153A IL35153A (en)	1969-09-25	1970-08-24	N-phenylcarboxylic acid amidines,their preparation and their use as acaricides

Country Status (8)

Country	Link
BE (1)	BE756571A (de)
CH (1)	CH537149A (de)
DE (1)	DE1948459B2 (de)
ES (1)	ES383385A1 (de)
FR (1)	FR2070087A1 (de)
IL (1)	IL35153A (de)
NL (1)	NL7014002A (de)
ZA (1)	ZA705951B (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU671071B2 (en) *	1990-08-30	1996-08-15	State of Oregon, acting by and through The Oregon State Board of Higher Education, acting for and on behalf of The Oregon Health Sciences University, Portland, Oregon, and The University of Oregon, Eugene, Oregon, Johnson Hall,	Substituted amidines having high binding to the sigma receptor and the use thereof

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL253634A (de) *	1959-07-10
BE629317A (de) *	1962-03-08
CH478522A (de) *	1966-07-05	1969-09-30	Ciba Geigy	Mittel gegen Ektoparasiten auf Tieren

0
- BE BE756571D patent/BE756571A/xx unknown
1969
- 1969-09-25 DE DE1948459A patent/DE1948459B2/de not_active Withdrawn
1970
- 1970-08-24 IL IL35153A patent/IL35153A/en unknown
- 1970-08-27 CH CH1285270A patent/CH537149A/de not_active IP Right Cessation
- 1970-08-31 ZA ZA705951*A patent/ZA705951B/xx unknown
- 1970-09-04 ES ES383385A patent/ES383385A1/es not_active Expired
- 1970-09-22 NL NL7014002A patent/NL7014002A/xx unknown
- 1970-09-25 FR FR7034888A patent/FR2070087A1/fr active Granted

Also Published As

Publication number	Publication date
IL35153A0 (en)	1970-10-30
DE1948459A1 (de)	1971-04-01
CH537149A (de)	1973-05-31
FR2070087B1 (de)	1974-08-23
ES383385A1 (es)	1973-02-16
FR2070087A1 (en)	1971-09-10
NL7014002A (de)	1971-03-29
DE1948459B2 (de)	1978-06-01
ZA705951B (en)	1971-05-27
BE756571A (fr)	1971-03-24

Publication	Publication Date	Title
US3995049A (en)	1976-11-30	Oxazolidine derivatives
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US4339448A (en)	1982-07-13	Imidazole-copper complex compounds and fungicides containing them
US4262005A (en)	1981-04-14	Compounds, compositions and methods for controlling pests
US4582849A (en)	1986-04-15	Fungicidal N-substituted maleic acid imides
IL35153A (en)	1974-09-10	N-phenylcarboxylic acid amidines,their preparation and their use as acaricides
EP0191514B1 (de)	1991-04-03	Imidazolderivate, Verfahren zu deren Herstellung und deren Anwendung als Fungizide
CS227695B2 (en)	1984-05-14	Fungicide
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CH619925A5 (en)	1980-10-31	Process for the preparation of 2-substituted benzanilide.
US4863966A (en)	1989-09-05	Pesticidal amines
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US4254133A (en)	1981-03-03	Combatting ectoparasites with phenylaminoalkyl-2-imidazoline compounds
US3697589A (en)	1972-10-10	N-(4-carboxy-benzylidene)amines
IL26594A (en)	1971-11-29	Molluscicidal preparations containing aliphatic nitrile compounds and certain novel aliphatic nitriles
US4011343A (en)	1977-03-08	Triazapentadienes as acaricides and insecticides
US4156017A (en)	1979-05-22	Pesticides
EP0254364B1 (de)	1991-09-11	Imidazol-Derivat
US4551458A (en)	1985-11-05	Quinazolines and fungicidal compositions thereof
EP0051884A1 (de)	1982-05-19	Aminocyclopropylcarboxylsäure-Derivate zum Lösen von Früchten und/oder Blättern von Pflanzen
US3751466A (en)	1973-08-07	N-benzylidene alkylamines