IL24814A - N',n'-disubstituted-thiono carbamyl thiolo-imides and process for their preparation - Google Patents

N',n'-disubstituted-thiono carbamyl thiolo-imides and process for their preparation

Info

Publication number: IL24814A
Authority: IL; Israel
Prior art keywords: compound; halogen; group; hydrogen; integer
Prior art date: 1964-12-22

Application number

IL24814A

Other languages

English (en)

Original Assignee

Roussel Uclaf

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.)

1964-12-22

Filing date

1965-12-16

Publication date

1971-04-28

1965-12-16 Application filed by Roussel Uclaf filed Critical Roussel Uclaf

1971-04-28 Publication of IL24814A publication Critical patent/IL24814A/en

Links

238000000034 method Methods 0.000 title claims description 13
238000002360 preparation method Methods 0.000 title description 12
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 40
125000000217 alkyl group Chemical group 0.000 claims description 15
229910052736 halogen Inorganic materials 0.000 claims description 13
150000002367 halogens Chemical class 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
125000003545 alkoxy group Chemical group 0.000 claims description 8
150000002431 hydrogen Chemical class 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
206010061217 Infestation Diseases 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims description 2
230000002538 fungal effect Effects 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
231100001184 nonphytotoxic Toxicity 0.000 claims description 2
125000006413 ring segment Chemical group 0.000 claims description 2
239000012871 anti-fungal composition Substances 0.000 claims 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 54
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
239000000047 product Substances 0.000 description 20
239000000243 solution Substances 0.000 description 17
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
238000013019 agitation Methods 0.000 description 14
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 11
239000000725 suspension Substances 0.000 description 11
239000000706 filtrate Substances 0.000 description 10
238000012360 testing method Methods 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
238000002844 melting Methods 0.000 description 9
230000008018 melting Effects 0.000 description 9
241000196324 Embryophyta Species 0.000 description 8
239000002244 precipitate Substances 0.000 description 8
238000011161 development Methods 0.000 description 7
230000018109 developmental process Effects 0.000 description 7
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
238000004458 analytical method Methods 0.000 description 6
235000013339 cereals Nutrition 0.000 description 5
229940032007 methylethyl ketone Drugs 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
238000011282 treatment Methods 0.000 description 5
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 4
PRFBKSLGIQOXST-UHFFFAOYSA-N 2-bromo-3a,4,5,6,7,7a-hexahydroisoindole-1,3-dione Chemical compound C1CCCC2C(=O)N(Br)C(=O)C21 PRFBKSLGIQOXST-UHFFFAOYSA-N 0.000 description 4
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 4
230000000843 anti-fungal effect Effects 0.000 description 4
238000004821 distillation Methods 0.000 description 4
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 4
230000000050 nutritive effect Effects 0.000 description 4
239000000843 powder Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000011734 sodium Substances 0.000 description 4
VHQBNQQGURPMOF-UHFFFAOYSA-N 2-bromo-5-chloroisoindole-1,3-dione Chemical compound ClC=1C=C2C(C(=O)N(C2=O)Br)=CC1 VHQBNQQGURPMOF-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
241000209140 Triticum Species 0.000 description 3
235000021307 Triticum Nutrition 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
238000001035 drying Methods 0.000 description 3
-1 ethyleniminyl Chemical group 0.000 description 3
239000007788 liquid Substances 0.000 description 3
125000002757 morpholinyl group Chemical group 0.000 description 3
244000045947 parasite Species 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
VMSRVIHUFHQIAL-UHFFFAOYSA-M sodium;n,n-dimethylcarbamodithioate Chemical compound [Na+].CN(C)C([S-])=S VMSRVIHUFHQIAL-UHFFFAOYSA-M 0.000 description 3
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 3
229960002317 succinimide Drugs 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
WLDMPODMCFGWAA-UHFFFAOYSA-N 3a,4,5,6,7,7a-hexahydroisoindole-1,3-dione Chemical compound C1CCCC2C(=O)NC(=O)C21 WLDMPODMCFGWAA-UHFFFAOYSA-N 0.000 description 2
241000233866 Fungi Species 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
229930182555 Penicillin Natural products 0.000 description 2
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
244000046052 Phaseolus vulgaris Species 0.000 description 2
241001533598 Septoria Species 0.000 description 2
240000003768 Solanum lycopersicum Species 0.000 description 2
239000011149 active material Substances 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
238000011109 contamination Methods 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
230000001408 fungistatic effect Effects 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
239000000203 mixture Substances 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
230000001473 noxious effect Effects 0.000 description 2
239000008188 pellet Substances 0.000 description 2
229940049954 penicillin Drugs 0.000 description 2
238000003756 stirring Methods 0.000 description 2
150000003573 thiols Chemical class 0.000 description 2
GATAOJICMOPURT-UHFFFAOYSA-N 2-pentan-3-yl-1-propylbenzimidazole Chemical compound C1=CC=C2N(CCC)C(C(CC)CC)=NC2=C1 GATAOJICMOPURT-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N 3-methyl-2-pentanone Chemical compound CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
ANENLORAJJKWAA-UHFFFAOYSA-N 4-bromoisoindole-1,3-dione Chemical compound BrC1=CC=CC2=C1C(=O)NC2=O ANENLORAJJKWAA-UHFFFAOYSA-N 0.000 description 1
BGJNRQSGJHVURK-UHFFFAOYSA-N 5-chloroisoindole-1,3-dione Chemical compound ClC1=CC=C2C(=O)NC(=O)C2=C1 BGJNRQSGJHVURK-UHFFFAOYSA-N 0.000 description 1
ANYWGXDASKQYAD-UHFFFAOYSA-N 5-nitroisoindole-1,3-dione Chemical compound [O-][N+](=O)C1=CC=C2C(=O)NC(=O)C2=C1 ANYWGXDASKQYAD-UHFFFAOYSA-N 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
241000223600 Alternaria Species 0.000 description 1
241000228197 Aspergillus flavus Species 0.000 description 1
241000221779 Fusarium sambucinum Species 0.000 description 1
235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
241000233614 Phytophthora Species 0.000 description 1
241000233622 Phytophthora infestans Species 0.000 description 1
241000233626 Plasmopara Species 0.000 description 1
241001281803 Plasmopara viticola Species 0.000 description 1
229920005372 Plexiglas® Polymers 0.000 description 1
229920001131 Pulp (paper) Polymers 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
241001136508 Talaromyces luteus Species 0.000 description 1
241000223261 Trichoderma viride Species 0.000 description 1
BSYMNHJUEWLOCC-UHFFFAOYSA-N [N+](=O)([O-])C=1C=C2C(C(=O)N(C2=O)Br)=CC1 Chemical compound [N+](=O)([O-])C=1C=C2C(C(=O)N(C2=O)Br)=CC1 BSYMNHJUEWLOCC-UHFFFAOYSA-N 0.000 description 1
238000009825 accumulation Methods 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000008272 agar Substances 0.000 description 1
QGLZXHRNAYXIBU-UHFFFAOYSA-N aldicarb Chemical compound CNC(=O)ON=CC(C)(C)SC QGLZXHRNAYXIBU-UHFFFAOYSA-N 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
244000309464 bull Species 0.000 description 1
DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical class NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000002131 composite material Substances 0.000 description 1
238000002788 crimping Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
230000001461 cytolytic effect Effects 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
238000009826 distribution Methods 0.000 description 1
239000000428 dust Substances 0.000 description 1
238000010410 dusting Methods 0.000 description 1
235000005489 dwarf bean Nutrition 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000010828 elution Methods 0.000 description 1
HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
230000035784 germination Effects 0.000 description 1
125000005462 imide group Chemical group 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000010899 nucleation Methods 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
238000010298 pulverizing process Methods 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
238000011160 research Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000002689 soil Substances 0.000 description 1
230000004763 spore germination Effects 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
QAZLUNIWYYOJPC-UHFFFAOYSA-M sulfenamide Chemical group [Cl-].COC1=C(C)C=[N+]2C3=NC4=CC=C(OC)C=C4N3SCC2=C1C QAZLUNIWYYOJPC-UHFFFAOYSA-M 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
239000003643 water by type Substances 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1
AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
- C07D209/72—4,7-Endo-alkylene-iso-indoles
- C07D209/76—4,7-Endo-alkylene-iso-indoles with oxygen atoms in positions 1 and 3
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
- C07D207/48—Sulfur atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Indole Compounds (AREA)

IL24814A 1964-12-22 1965-12-16 N',n'-disubstituted-thiono carbamyl thiolo-imides and process for their preparation IL24814A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR999589A FR1439872A (fr)	1964-12-22	1964-12-22	Nouveaux composés dithiocarbamiques et procédé de préparation
FR33455A FR90155E (fr)	1964-12-22	1965-10-01	Nouveaux composés dithiocarbamiques et procédé de préparation

Publications (1)

Publication Number	Publication Date
IL24814A true IL24814A (en)	1971-04-28

Family

ID=26166513

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL24814A IL24814A (en)	1964-12-22	1965-12-16	N',n'-disubstituted-thiono carbamyl thiolo-imides and process for their preparation

Country Status (7)

Country	Link
US (1)	US3410842A (fr)
CH (1)	CH455792A (fr)
DE (1)	DE1567059A1 (fr)
FR (2)	FR1439872A (fr)
GB (1)	GB1077180A (fr)
IL (1)	IL24814A (fr)
NL (1)	NL6516691A (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1670881A1 (de) *	1967-06-13	1971-03-25	Bayer Ag	Verfahren zur Herstellung von Phthalimidomethylisothiocyanat
US3928340A (en) *	1972-06-26	1975-12-23	Goodyear Tire & Rubber	N-{8 (Substituted amino) thio{9 -imides
US4042701A (en) *	1975-09-22	1977-08-16	Ciba-Geigy Corporation	7,7-Diphenyl-1,4-oxazepinoalkyl-dicarboximides
US4264502A (en) *	1979-03-09	1981-04-28	Gulf Oil Corporation	N-(arylthiocarbamoyl)-2-amino-1H-isoindole-1,3-(2H)diones and use as plant growth regulators
US4292071A (en) *	1979-05-03	1981-09-29	Gulf Oil Corporation	Isothioureido isoindolediones and use as plant growth regulators
US4272284A (en) *	1980-03-13	1981-06-09	Gulf Oil Corporation	Arylthioureidoisoindolines and use as plant growth regulators
US4289527A (en)	1980-08-04	1981-09-15	Gulf Oil Corporation	Plant growth regulating perfluoroacyl arylthioureido isoindolediones
US5228899A (en) *	1989-08-25	1993-07-20	Sumitomo Chemical Company Limited	Hydroxamic acid esters and plant growth regulation therewith
US5237067A (en) *	1992-02-04	1993-08-17	Schumaker Robert R	Optoelectronic tautomeric compositions

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3371085A (en) *	1959-12-10	1968-02-27	Hoffmann La Roche	5-aryl-3h-1,4-benzodiazepin-2(1h)-ones

1964
- 1964-12-22 FR FR999589A patent/FR1439872A/fr not_active Expired
1965
- 1965-10-01 FR FR33455A patent/FR90155E/fr not_active Expired
- 1965-12-10 DE DE19651567059 patent/DE1567059A1/de active Pending
- 1965-12-14 US US513859A patent/US3410842A/en not_active Expired - Lifetime
- 1965-12-16 IL IL24814A patent/IL24814A/en unknown
- 1965-12-21 CH CH1756165A patent/CH455792A/fr unknown
- 1965-12-22 NL NL6516691A patent/NL6516691A/xx unknown
- 1965-12-22 GB GB54382/65A patent/GB1077180A/en not_active Expired

Also Published As

Publication number	Publication date
FR1439872A (fr)	1966-05-27
CH455792A (fr)	1968-05-15
GB1077180A (en)	1967-07-26
NL6516691A (fr)	1966-06-23
FR90155E (fr)	1967-10-27
DE1567059A1 (de)	1970-05-27
US3410842A (en)	1968-11-12

Publication	Publication Date	Title
DE2513732C2 (fr)	1988-04-14
EP0313512B1 (fr)	1992-11-25	Benzothiadiazoles et leur utilisation dans des procédés et des compositions contre les maladies végétales
GB2024824A (en)	1980-01-16	Cyanopyrrole derivatives
DE2741437C2 (fr)	1987-11-05
IL24814A (en)	1971-04-28	N',n'-disubstituted-thiono carbamyl thiolo-imides and process for their preparation
DE2626063A1 (de)	1977-12-22	Fungizide bzw. bakterizide 2,3-dihydro-1,4-dithiin-1,1,4,4-tetroxide und deren verwendung
CN109956904B (zh)	2022-03-01	吡唑酰胺类化合物及其应用和杀菌剂
US3098002A (en)	1963-07-16	Method of controlling fungi and algae with nu-phenyl-itaconimides
EP0387195A1 (fr)	1990-09-12	Agents pour la protection des plantes contre des maladies
US3978217A (en)	1976-08-31	Water-soluble 1 and/or 2 acid alkylene imidazoles
JPS62281886A (ja)	1987-12-07	フオスフアイト誘導体及びその製造方法
US4035387A (en)	1977-07-12	1,3-Dithiol-2-ylidene malonic esters
DE1670709A1 (de)	1970-12-03	Pestizide Mittel
DE2128700C2 (de)	1985-04-25	Fungitoxische Mittel
Wain et al.	1963	Investigations on fungicides: VIII. The fungicidal properties of some thiocarbamoylthionitroparaffins
US4049820A (en)	1977-09-20	Substituted urazole and thiourazole compounds as agricultural fungicidal agents
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