CA1092609A - N.sub.1-chloro-3,5-dinitrosulfanilamides - Google Patents

N.sub.1-chloro-3,5-dinitrosulfanilamides

Info

Publication number: CA1092609A
Authority: CA; Canada
Prior art keywords: compound; formula; chloro; dinitro; sodium salt
Prior art date: 1976-12-09
Legal status (The legal status 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 status listed.): Expired

Application number

CA292,470A

Other languages

English (en)

French (fr)

Inventor

James R. Beck

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Eli Lilly and Co

Original Assignee

Eli Lilly and Co

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.)

1976-12-09

Filing date

1977-12-06

Publication date

1980-12-30

1977-12-06 Application filed by Eli Lilly and Co filed Critical Eli Lilly and Co

1980-12-30 Application granted granted Critical

1980-12-30 Publication of CA1092609A publication Critical patent/CA1092609A/en

Status Expired legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims abstract description 106
241000196324 Embryophyta Species 0.000 claims abstract description 12
240000006365 Vitis vinifera Species 0.000 claims abstract description 8
235000014787 Vitis vinifera Nutrition 0.000 claims abstract description 8
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 claims abstract description 7
241000233679 Peronosporaceae Species 0.000 claims abstract description 7
235000009754 Vitis X bourquina Nutrition 0.000 claims abstract description 7
235000012333 Vitis X labruscana Nutrition 0.000 claims abstract description 7
230000002363 herbicidal effect Effects 0.000 claims abstract description 7
229910052708 sodium Inorganic materials 0.000 claims abstract description 7
239000011734 sodium Substances 0.000 claims abstract description 7
238000000034 method Methods 0.000 claims description 34
159000000000 sodium salts Chemical class 0.000 claims description 29
239000002904 solvent Substances 0.000 claims description 19
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims description 10
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
-1 N1-chloro-3,5-dinitrosulfanilamide compound Chemical class 0.000 claims description 8
239000005708 Sodium hypochlorite Substances 0.000 claims description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 6
229940124530 sulfonamide Drugs 0.000 claims description 5
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
125000005394 methallyl group Chemical group 0.000 claims description 4
FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 4
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
230000000855 fungicidal effect Effects 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
229910052700 potassium Chemical group 0.000 claims description 2
239000011591 potassium Chemical group 0.000 claims description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 7
BABLIQYVOXZZFA-UHFFFAOYSA-N 4-[butyl(ethyl)amino]-N-chloro-3,5-dinitrobenzenesulfonamide Chemical compound C(CCC)N(C1=C(C=C(S(=O)(=O)NCl)C=C1[N+](=O)[O-])[N+](=O)[O-])CC BABLIQYVOXZZFA-UHFFFAOYSA-N 0.000 claims 3
GAXYNMUELWLDPW-UHFFFAOYSA-N N-chloro-4-(dipropylamino)-3,5-dinitrobenzenesulfonamide Chemical compound ClNS(=O)(C1=CC(=C(C(=C1)[N+](=O)[O-])N(CCC)CCC)[N+](=O)[O-])=O GAXYNMUELWLDPW-UHFFFAOYSA-N 0.000 claims 3
SJBMTLSYJLRWTQ-UHFFFAOYSA-N N-chloro-4-[cyclopropylmethyl(propyl)amino]-3,5-dinitrobenzenesulfonamide Chemical compound ClNS(=O)(C1=CC(=C(C(=C1)[N+](=O)[O-])N(CCC)CC1CC1)[N+](=O)[O-])=O SJBMTLSYJLRWTQ-UHFFFAOYSA-N 0.000 claims 3
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 3
159000000001 potassium salts Chemical class 0.000 abstract description 6
241000233866 Fungi Species 0.000 abstract description 3
230000003389 potentiating effect Effects 0.000 abstract description 2
FARHXWKUXJFLIF-UHFFFAOYSA-N 4-amino-N-chloro-3,5-dinitrobenzenesulfonamide Chemical class ClNS(=O)(C1=CC(=C(C(=C1)[N+](=O)[O-])N)[N+](=O)[O-])=O FARHXWKUXJFLIF-UHFFFAOYSA-N 0.000 abstract 1
239000000203 mixture Substances 0.000 description 31
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
238000012360 testing method Methods 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000002689 soil Substances 0.000 description 12
239000000243 solution Substances 0.000 description 12
239000007788 liquid Substances 0.000 description 9
239000002270 dispersing agent Substances 0.000 description 7
229960005076 sodium hypochlorite Drugs 0.000 description 7
NGGSHOMDJNQYEZ-UHFFFAOYSA-N 4-amino-3,5-dinitrobenzenesulfonamide Chemical class NC1=C([N+]([O-])=O)C=C(S(N)(=O)=O)C=C1[N+]([O-])=O NGGSHOMDJNQYEZ-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
201000010099 disease Diseases 0.000 description 6
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
239000000428 dust Substances 0.000 description 6
239000000047 product Substances 0.000 description 6
239000000126 substance Substances 0.000 description 5
NIDOTDANGJJHPU-UHFFFAOYSA-N 4-amino-2-chlorobenzenesulfonamide Chemical compound NC1=CC=C(S(N)(=O)=O)C(Cl)=C1 NIDOTDANGJJHPU-UHFFFAOYSA-N 0.000 description 4
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
238000001914 filtration Methods 0.000 description 4
238000010348 incorporation Methods 0.000 description 4
239000003921 oil Substances 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
239000007787 solid Substances 0.000 description 4
QFUSCYRJMXLNRB-UHFFFAOYSA-N 2,6-dinitroaniline Chemical class NC1=C([N+]([O-])=O)C=CC=C1[N+]([O-])=O QFUSCYRJMXLNRB-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
240000006122 Chenopodium album Species 0.000 description 3
235000009344 Chenopodium album Nutrition 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000002518 antifoaming agent Substances 0.000 description 3
239000000969 carrier Substances 0.000 description 3
239000008367 deionised water Substances 0.000 description 3
229910021641 deionized water Inorganic materials 0.000 description 3
239000007921 spray Substances 0.000 description 3
239000004094 surface-active agent Substances 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
235000013479 Amaranthus retroflexus Nutrition 0.000 description 2
241000209764 Avena fatua Species 0.000 description 2
235000007320 Avena fatua Nutrition 0.000 description 2
229920000742 Cotton Polymers 0.000 description 2
240000008067 Cucumis sativus Species 0.000 description 2
240000008853 Datura stramonium Species 0.000 description 2
244000068988 Glycine max Species 0.000 description 2
235000010469 Glycine max Nutrition 0.000 description 2
241000219146 Gossypium Species 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
240000007594 Oryza sativa Species 0.000 description 2
235000007164 Oryza sativa Nutrition 0.000 description 2
241001281803 Plasmopara viticola Species 0.000 description 2
240000005498 Setaria italica Species 0.000 description 2
235000011684 Sorghum saccharatum Nutrition 0.000 description 2
244000062793 Sorghum vulgare Species 0.000 description 2
241000209140 Triticum Species 0.000 description 2
235000021307 Triticum Nutrition 0.000 description 2
240000008042 Zea mays Species 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
229940075894 denatured ethanol Drugs 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
238000009472 formulation Methods 0.000 description 2
239000010440 gypsum Substances 0.000 description 2
229910052602 gypsum Inorganic materials 0.000 description 2
239000004009 herbicide Substances 0.000 description 2
208000015181 infectious disease Diseases 0.000 description 2
238000011081 inoculation Methods 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
230000000361 pesticidal effect Effects 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
239000004033 plastic Substances 0.000 description 2
239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 2
235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 2
229910052903 pyrophyllite Inorganic materials 0.000 description 2
241000894007 species Species 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
LQRUJQAAPFZOIR-UHFFFAOYSA-N 4-[cyclopropylmethyl(propyl)amino]-3,5-dinitrobenzenesulfonamide Chemical compound [O-][N+](=O)C=1C=C(S(N)(=O)=O)C=C([N+]([O-])=O)C=1N(CCC)CC1CC1 LQRUJQAAPFZOIR-UHFFFAOYSA-N 0.000 description 1
244000237956 Amaranthus retroflexus Species 0.000 description 1
235000004135 Amaranthus viridis Nutrition 0.000 description 1
235000004535 Avena sterilis Nutrition 0.000 description 1
235000021533 Beta vulgaris Nutrition 0.000 description 1
241000335053 Beta vulgaris Species 0.000 description 1
241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
241000905957 Channa melasoma Species 0.000 description 1
235000005484 Chenopodium berlandieri Nutrition 0.000 description 1
235000009332 Chenopodium rubrum Nutrition 0.000 description 1
235000009849 Cucumis sativus Nutrition 0.000 description 1
235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
241000192043 Echinochloa Species 0.000 description 1
244000058871 Echinochloa crus-galli Species 0.000 description 1
240000000047 Gossypium barbadense Species 0.000 description 1
235000009429 Gossypium barbadense Nutrition 0.000 description 1
229920001213 Polysorbate 20 Polymers 0.000 description 1
235000007226 Setaria italica Nutrition 0.000 description 1
235000015505 Sorghum bicolor subsp. bicolor Nutrition 0.000 description 1
235000021536 Sugar beet Nutrition 0.000 description 1
208000027418 Wounds and injury Diseases 0.000 description 1
235000007244 Zea mays Nutrition 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
229940008309 acetone / ethanol Drugs 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
239000000440 bentonite Substances 0.000 description 1
229910000278 bentonite Inorganic materials 0.000 description 1
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
239000004568 cement Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
230000006378 damage Effects 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
239000004495 emulsifiable concentrate Substances 0.000 description 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
239000013020 final formulation Substances 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
125000001475 halogen functional group Chemical group 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
208000006278 hypochromic anemia Diseases 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
208000014674 injury Diseases 0.000 description 1
239000011872 intimate mixture Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
238000002156 mixing Methods 0.000 description 1
LZGUHMNOBNWABZ-UHFFFAOYSA-N n-nitro-n-phenylnitramide Chemical compound [O-][N+](=O)N([N+]([O-])=O)C1=CC=CC=C1 LZGUHMNOBNWABZ-UHFFFAOYSA-N 0.000 description 1
UNAHYJYOSSSJHH-UHFFFAOYSA-N oryzalin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(S(N)(=O)=O)C=C1[N+]([O-])=O UNAHYJYOSSSJHH-UHFFFAOYSA-N 0.000 description 1
235000002252 panizo Nutrition 0.000 description 1
238000003359 percent control normalization Methods 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
230000003032 phytopathogenic effect Effects 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
238000004382 potting Methods 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
208000024891 symptom Diseases 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
- 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
- A01N41/04—Sulfonic acids; Derivatives thereof
- A01N41/06—Sulfonic acid amides

Landscapes

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

CA292,470A 1976-12-09 1977-12-06 N.sub.1-chloro-3,5-dinitrosulfanilamides Expired CA1092609A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US748,856		1976-12-09
US05/748,856 US4104054A (en)	1976-12-09	1976-12-09	N1 -chloro-3,5-dinitrosulfanilamides

Publications (1)

Publication Number	Publication Date
CA1092609A true CA1092609A (en)	1980-12-30

Family

ID=25011223

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA292,470A Expired CA1092609A (en)	1976-12-09	1977-12-06	N.sub.1-chloro-3,5-dinitrosulfanilamides

Country Status (12)

Country	Link
US (1)	US4104054A (2)
JP (1)	JPS5373539A (2)
BE (1)	BE861475A (2)
BR (1)	BR7708157A (2)
CA (1)	CA1092609A (2)
DE (1)	DE2754053A1 (2)
FR (1)	FR2373524A1 (2)
GB (1)	GB1589943A (2)
IE (1)	IE45849B1 (2)
IL (1)	IL53527A (2)
IT (1)	IT1088587B (2)
NL (1)	NL7713453A (2)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1994024253A1 (en) *	1993-04-20	1994-10-27	Ecolab Inc.	Novel low foaming rinse agents comprising alkylene oxide modified sorbitol fatty acid ester and defoaming agent
WO2003090678A2 (en) *	2002-04-23	2003-11-06	Ohio State University	Antileishmanial dinitroaniline sulfonamides with activity against parasite tubulin
US7824448B2 (en) *	2002-11-22	2010-11-02	Schneider David J	Process for stain removal

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR766577A (fr) *	1933-03-31	1934-06-30	Chlorosoda	Procédé d'obtention de composés organiques générateurs de chlore actif
US2328455A (en) *	1942-07-02	1943-08-31	American Cyanamid Co	N-alkali metal-n, n-dihalogen acylsulphanilamides
NL132336C (2) *	1951-01-28

1976
- 1976-12-09 US US05/748,856 patent/US4104054A/en not_active Expired - Lifetime
1977
- 1977-12-02 IL IL53527A patent/IL53527A/xx unknown
- 1977-12-02 GB GB50244/77A patent/GB1589943A/en not_active Expired
- 1977-12-05 FR FR7736590A patent/FR2373524A1/fr active Granted
- 1977-12-05 IT IT30390/77A patent/IT1088587B/it active
- 1977-12-05 BE BE1008559A patent/BE861475A/xx unknown
- 1977-12-05 DE DE19772754053 patent/DE2754053A1/de not_active Withdrawn
- 1977-12-06 NL NL7713453A patent/NL7713453A/xx not_active Application Discontinuation
- 1977-12-06 CA CA292,470A patent/CA1092609A/en not_active Expired
- 1977-12-08 IE IE2494/77A patent/IE45849B1/en unknown
- 1977-12-08 BR BR7708157A patent/BR7708157A/pt unknown
- 1977-12-09 JP JP14868377A patent/JPS5373539A/ja active Pending

Also Published As

Publication number	Publication date
BR7708157A (pt)	1978-08-15
DE2754053A1 (de)	1978-06-15
GB1589943A (en)	1981-05-20
IT1088587B (it)	1985-06-10
FR2373524B1 (2)	1980-09-19
NL7713453A (nl)	1978-06-13
IL53527A (en)	1981-03-31
IL53527A0 (en)	1978-03-10
IE45849L (en)	1978-06-09
IE45849B1 (en)	1982-12-15
FR2373524A1 (fr)	1978-07-07
US4104054A (en)	1978-08-01
BE861475A (fr)	1978-06-05
JPS5373539A (en)	1978-06-30

Legal Events

Date	Code	Title	Description
1997-12-30	MKEX	Expiry

Publication	Publication Date	Title
JPS6052146B2 (ja)	1985-11-18	Ｎ−ピリジルアニリン系化合物、それらの製造方法及びそれらを含有する有害生物防除剤
AU2022310707A1 (en)	2024-01-25	Herbicidal phenyluracils
DD219654A5 (de)	1985-03-13	Fungizides mittel fuer die llandwirtschaft und den gartenbaubetrieb und verfahren zurbekaempfung von pflanzenkrankheiten
PL155723B1 (en)	1991-12-31	Pesticide in particular against insects, nematodes and mites
CA1092609A (en)	1980-12-30	N.sub.1-chloro-3,5-dinitrosulfanilamides
JPH0768205B2 (ja)	1995-07-26	ベンゾイル尿素誘導体およびそれを有効成分とする殺虫剤
KR920001469B1 (ko)	1992-02-14	테트라히드로피리미딘 유도체
JPH0421672B2 (2)	1992-04-13
US4904301A (en)	1990-02-27	5-Fluoromethyl-1,2,4-triazolo(1,5-A)-pyrimidines
JPS599545B2 (ja)	1984-03-03	アシル尿素、その製造法及び該化合物を含有する殺虫剤
CN118702674A (zh)	2024-09-27	一种含哒嗪酮的2-苯基吡啶衍生物及其合成方法和应用
JPH0517220B2 (2)	1993-03-08
PL120535B1 (en)	1982-03-31	Pesticide or plant growth regulator and process for manufacturing sulfonanilidesenijj i sposob poluchenija sul'fonanilidov
US4049820A (en)	1977-09-20	Substituted urazole and thiourazole compounds as agricultural fungicidal agents
RU2038352C1 (ru)	1995-06-27	Производные амина или их соли и инсектицидная композиция на их основе
EP0003430A1 (en)	1979-08-08	Novel 2,6-dinitrobenzenamines, their preparation, composition containing them and their use as fungicides
JPS63227502A (ja)	1988-09-21	防菌防カビ剤
CS232736B2 (en)	1985-02-14	Fungicide agent and method of active component production
CA1048042A (en)	1979-02-06	Thiocyano-xanthate biocides and miticides
US4758263A (en)	1988-07-19	2-(2,5-difluorophenyl)-4-methyl-1,2,4-oxadiazolidine-3,5 diones
JPH02503924A (ja)	1990-11-15	５‐フルオロメチル‐１，２，４‐トリアゾロ〔１，５‐ａ〕ピリミジン‐２‐スルホンアミド類，それらの調製方法及び除草剤としてそれらを使用するための組成物
US4153730A (en)	1979-05-08	Fungicidal and herbicidal methods
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JPH07242665A (ja)	1995-09-19	フルオロプロピルチアゾリン誘導体及び除草剤
EP1364951B1 (en)	2012-05-02	Triazoquinolone derivatives as pest controllers