DE3220883C2 - Salts of N- (4-trifluoromethylphenyl) tetrachlorophthalamic acid, process for their preparation and their use as pesticides - Google Patents
Salts of N- (4-trifluoromethylphenyl) tetrachlorophthalamic acid, process for their preparation and their use as pesticidesInfo
- Publication number
- DE3220883C2 DE3220883C2 DE3220883A DE3220883A DE3220883C2 DE 3220883 C2 DE3220883 C2 DE 3220883C2 DE 3220883 A DE3220883 A DE 3220883A DE 3220883 A DE3220883 A DE 3220883A DE 3220883 C2 DE3220883 C2 DE 3220883C2
- Authority
- DE
- Germany
- Prior art keywords
- acid
- salts
- trifluoromethylphenyl
- tetrachlorophthalamic
- formula
- Prior art date
- 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
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 25
- YMTDTSSUEXTEJZ-UHFFFAOYSA-N 2,3,4,5-tetrachloro-6-[[4-(trifluoromethyl)phenyl]carbamoyl]benzoic acid Chemical class OC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(=O)NC1=CC=C(C(F)(F)F)C=C1 YMTDTSSUEXTEJZ-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 238000000034 method Methods 0.000 title claims description 17
- 238000002360 preparation method Methods 0.000 title claims description 6
- 239000000575 pesticide Substances 0.000 title abstract description 4
- 239000002253 acid Substances 0.000 claims abstract description 21
- 229910001385 heavy metal Chemical class 0.000 claims abstract description 12
- 239000003513 alkali Substances 0.000 claims abstract description 7
- 150000003863 ammonium salts Chemical class 0.000 claims abstract 2
- 159000000003 magnesium salts Chemical class 0.000 claims description 4
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 150000003751 zinc Chemical class 0.000 claims description 2
- 150000002696 manganese Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 7
- ZICLFCRMXFSOHC-UHFFFAOYSA-N 2-[[4-(trifluoromethyl)phenyl]carbamoyl]benzoic acid Chemical class OC(=O)C1=CC=CC=C1C(=O)NC1=CC=C(C(F)(F)F)C=C1 ZICLFCRMXFSOHC-UHFFFAOYSA-N 0.000 abstract description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical class [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000908 ammonium hydroxide Substances 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 9
- -1 ammonium radical Chemical class 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 241000196324 Embryophyta Species 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 230000000844 anti-bacterial effect Effects 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000005554 pickling Methods 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- VLHPTNVVTJTDHN-UHFFFAOYSA-N 2-carbamoyl-3,4,5,6-tetrachlorobenzoic acid Chemical class NC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(O)=O VLHPTNVVTJTDHN-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000004606 Fillers/Extenders Substances 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
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- 229910052725 zinc Inorganic materials 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
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- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000588921 Enterobacteriaceae Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- WAEMQWOKJMHJLA-UHFFFAOYSA-N Manganese(2+) Chemical compound [Mn+2] WAEMQWOKJMHJLA-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
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- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
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- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
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- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
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- 238000010790 dilution Methods 0.000 description 1
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- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
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- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical class [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
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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
- A01N37/18—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 the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/30—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 the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the groups —CO—N< and, both being directly attached by their carbon atoms to the same carbon skeleton, e.g. H2N—NH—CO—C6H4—COOCH3; Thio-analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/04—Nickel compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/02—Iron compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
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Abstract
Die vorliegende Erfindung betrifft neue Salze der N-(4-Trifluormethylphenyl)-tetrachlorphthalamidsäure der Formel (I) (Formel I) in welcher M für ein Alkali-, Erdalkali-, gegebenenfalls substituiertes Ammonium oder Schwermetalläquivalent steht. Sie werden aus der freien Säure durch Umsetzung mit Alkali-, Erdalkali- oder gegebenenfalls substituierten Ammoniumhydroxid erhalten. Die Schwermetallsalze werden aus wasserlöslichen Salzen durch Zugabe entsprechender Schwermetallsalze hergestellt. Die neuen Salze der N-(4-Trifluormethylphenyl)-phthalamidsäure können als Schädlingsbekämpfungsmittel eingesetzt werden und zeichnen sich durch eine hohe Wirksamkeit und Wirkungsdauer aus.The present invention relates to new salts of N- (4-trifluoromethylphenyl) tetrachlorophthalamic acid of the formula (I) (formula I) in which M stands for an alkali, alkaline earth, optionally substituted ammonium or heavy metal equivalent. They are obtained from the free acid by reaction with alkali, alkaline earth or optionally substituted ammonium hydroxide. The heavy metal salts are made from water-soluble salts by adding corresponding heavy metal salts. The new salts of N- (4-trifluoromethylphenyl) phthalamic acid can be used as pesticides and are distinguished by their high effectiveness and duration of action.
Description
a) die N-(4-Trifluorrnethylphenyl)-tetrachlorphthalamidsäure der Formel (II)a) N- (4-trifluoromethylphenyl) -tetrachlorophthalamic acid of the formula (II)
CO —OHCO-OH
mit einer Verbindung der Formel (NI)with a compound of the formula (NI)
X — OH (Π)X - OH (Π)
in welcherin which
X für ein Alkali-, Erdalkali- oder gegebenenfalls substituiertes Ammoniumkation steht, in Gegenwart eines Verdünnungs- oder Lösungsmittels umsetzt, oder b) die wasserlöslichen Salze der N-(4-Trifluormethylphenyl)-tetrachlorphthalamidsäure der Formel (IV)X stands for an alkali, alkaline earth or optionally substituted ammonium cation, reacts in the presence of a diluent or solvent, or b) the water-soluble salts of N- (4-trifluoromethylphenyl) tetrachlorophthalamic acid of the formula (IV)
CO-OXCO-OX
CO —NH-< >—CF3 (IV)CO —NH- <> —CF 3 (IV)
in welcherin which
X die angegebene Bedeutung hat,X has the meaning given,
mit einem Schwermetallsalz der Formel (V)with a heavy metal salt of the formula (V)
Y-Z (V)Y-Z (V)
in welcherin which
Y für ein Schwermetalläquivalent und
Z für ein Anion stehen,Y for a heavy metal equivalent and
Z stand for an anion,
in wäßriger Lösung umsetzt.converts in aqueous solution.
8. Verwendung von Salzen der N-(4-Trifluormethylphenyl)-tetrachlorphthalamidsäure gemäß den Ansprüchen 1 bis 6 zur Bekämpfung von Schädlingen.8. Use of salts of N- (4-trifluoromethylphenyl) tetrachlorophthalamic acid according to the claims 1 to 6 for pest control.
Die vorliegende Erfindung betrifft neue Salze der N-(4-Trifluormethylphenyl)-tetrachiorphthalamidsäure, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Schädlingsbekämpfungsmittel.The present invention relates to new salts of N- (4-trifluoromethylphenyl) -tetrachiorphthalamic acid, Process for their manufacture and their use as pesticides.
Es ist bereits bekannt geworden, daß Tetrachlorphthalamidsäuren, z. B. eine pflanzenbakterizide Wirkung besitzen. So zeigt die N-(2,3-Dichlorphenyl)-tetrachlorphthalamidsäure eine bakterizide Wirkung gegen Xanrhomonas orvzae im Reis (vgl. GB-PS 13 55 849). Aus dergleichen Stoffklasse besitzt die N-(4-TrifluormethylphenyU-tetrachlorphthalamidsäure ebenfalls eine gute bakterizide Wirkung (vgl. DE-OS 29 32 689).It is already known that tetrachlorophthalamic acids, e.g. B. a plant bactericidal effect own. For example, N- (2,3-dichlorophenyl) -tetrachlorophthalamic acid has a bactericidal effect against Xanrhomonas orvzae in rice (see GB-PS 13 55 849). N- (4-trifluoromethylphenyU-tetrachlorophthalamic acid belongs to the same class of substances also a good bactericidal effect (cf. DE-OS 29 32 689).
Es wurden die neuen Salze der N-(4-Trifluormethylphenyl)-phthalamidsäure der Formel (I) 5There were the new salts of N- (4-trifluoromethylphenyl) phthalamic acid of the formula (I) 5
Cl
Cl COOMCl
Cl COOM
CONH-^f ^CF3 (DCONH- ^ f ^ CF 3 (D
ClCl
in welcher l: in which l:
M für ein Alkali-, Erdalkali- oder Schwermetalläquivalent oder für einen gegebenenfalls substituierten Ammoniumrest
steht,
gefunden.
Weiterhin wurde gefunden, daß man die neuen Saize der N-H-TrifluormethylphenylHetrachlorphthalamid-M stands for an alkali, alkaline earth or heavy metal equivalent or for an optionally substituted ammonium radical,
found.
It has also been found that the new Saize of NH-TrifluormethylphenylHetrachlorphthalamid-
säure der Formel d) 20 acid of formula d) 20
Cl
Cl I COOMCl
Cl I COOM
CICI
in welcher "°in which "°
M für ein Alkali-, L;dalkali- oder Schwermetalläquivalent oder für einen gegebenenlalls substituierten Ammoniumrest
steht,
erhält, wenn manM stands for an alkali, L; dalkali or heavy metal equivalent or for an optionally substituted ammonium radical,
received when one
a) die N-(4-Trif!uormethylphenyl)-tütrachlorphthalamidsäure der Formel (II) .'5a) N- (4-trifluoromethylphenyl) -tetrachlorophthalamic acid of the formula (II) .'5
ClCl
COOHCOOH
C/Y\o-NH^VCF·
r·! N=/ C / Y \ o-NH ^ V CF
r ·! N = /
Cl I CO —NH-<f ^CF3 (Π)Cl I CO —NH- <f ^ CF 3 (Π)
Cl ^=/Cl ^ = /
mit einer Verbindung der Formel (III) 45 with a compound of formula (III) 45
X-OH (CT)X-OH (CT)
in welcherin which
X Tür ein Alkali-, Erdalkali- oder gegebenenlalls substituiertes Ammoniumkation steht, 50X denotes an alkali, alkaline earth or optionally substituted ammonium cation, 50
in Gegenwart eines Verdünnungs- oder Lösungsmittels umsetzt, oder wenn man b) die wasserlöslichen Salze der N-H-TrifluormethylphenyD-tetrachlorphthalamidsäure der Formel (IV)in the presence of a diluent or solvent, or if one b) the water-soluble salts of N-H-trifluoromethylphenyD-tetrachlorophthalamic acid of the formula (IV)
COOX 55 COOX 55
Cl T CO —NH-ζ^—CF, (IV) m Cl T CO -NH-ζ ^ -CF, (IV) m
in welcherin which
X die angegebene Bedeutung hat,X has the meaning given,
mit einem Schwermetallsalz der Formel (V)with a heavy metal salt of the formula (V)
Y-Z (V)Y-Z (V)
in welcherin which
Y die oben angegebene Bedeutung hat und
Z tür ein Anion steht,Y has the meaning given above and
Z stands for an anion,
in wäßriger Lösung umsetzt.converts in aqueous solution.
Die neuen Salze der N-[4-Trifluormethylphenyl]-tetrachlorphthaIamidsäure weisen vor allem eine starke bakterizide Wirkung auf. Dabei ist es überraschend, daß die erfindungsgemäßen Verbindungen eine gleiche oder zum Teil bessere Wirkung und vor allem längere Wirkungsdauer gegen pflanzenschädigende Bakterien aufweisen als die aus dem Stand der Technik vorbekannte, gut wirksame freie Säure, die N-[4-TrifIuormethylphenyl]-tetrachloiphthalamidsäure. Bei der freien Säure als solche und in ihren Formulierungen wurden Abbauerscheinungen bereits bei Zimmertemperatur registriert. Nach 8 Wochen bei 400C wurden Wirkungsverluste von über 30". beobachtet, da die freie Säure zu dem nur wenig wirksamen Dicarbonsäureimidderivat cyclisiert.The new salts of N- [4-trifluoromethylphenyl] -tetrachlorophthalamic acid mainly have a strong bactericidal effect. It is surprising that the compounds according to the invention have the same or in some cases better action and, above all, a longer duration of action against plant-damaging bacteria than the well-active free acid known from the prior art, N- [4-trifluoromethylphenyl] -tetrachloiphthalamic acid. In the case of the free acid as such and in its formulations, signs of degradation were already registered at room temperature. After 8 weeks at 40 ° C., losses of activity of more than 30 ″ were observed, since the free acid cyclizes to form the dicarboximide derivative which is only slightly active.
Die neuen Verbindungen stellen aufgrund ihrergleich guten oder zum Teil besseren Wirkung und ihrer hohen Lagerstabilität eine Bereicherung der Technik dar.The new compounds because of their equally good or partly better effect and their high Storage stability is an enrichment of the technology.
Die erllndungsgemäßen Salze der N-^-Trifluormethylphenyll-tetrachlorphthalamidsäure sind durch die Formel (I) definiert.The salts of the N - ^ - trifluoromethylphenyl-tetrachlorophthalamic acid according to the invention are represented by the formula (I) defined.
Vorzugsweise seien genannt:The following are preferably mentioned:
das Kaliumsalz der N-^-TrilluormethylphenvIl-tetrachlorphthalamidsäure, das Magnesiumsalz der N-^-Trilluormethylphenylj-tetrachlorphthalamidsäure, das Kupfersalz der N-[4-Trinuormethylphenyi]-tetrach!orphthalamidsäure, das Marigansaiz der N-^-Triiliiurmethyiphenyij-ieirachiorphthalamidsäurc und das Zinksalz der N-[4-Trinuorrne*iiylphenyl]-tetrachlorphtharamidsäure.the potassium salt of N - ^ - trilluormethylphenvIl-tetrachlorophthalamic acid, the magnesium salt of N - ^ - trilluomethylphenylj-tetrachlorophthalamic acid, the copper salt of N- [4-Trinuormethylphenyi] -tetrach! orphthalamic acid, das Marigansaiz der N - ^ - Triiliiurmethyiphenyij-ieirachiorphthalamidsäurc and the zinc salt of N- [4-Trinuorrne * iiylphenyl] -tetrachlorophtharamic acid.
Verwendet man z.B. bei der Veirfahrensvariante a) N-^-Trifiuormethylphenyll-tetrachlorphthalamidsäure und Natriumhydroxid als Ausgangsmaterialien, so kann der Reaktionsvcrlauf durch das folgende Formelschema wiedergegeben werden:If, for example, in process variant a) N - ^ - trifluoromethylphenyl tetrachlorophthalamic acid is used and sodium hydroxide as starting materials, the reaction can be represented by the following equation be reproduced:
CO-OHCO-OH
+ NaOH+ NaOH
Verwendet man z. B. bei der Verfahrensvariante b) das Kaliumsalz der N-[4-Trifluormethylpnenyl]-tetrachlorphthalamidsäure und Zinkchiorid als Ausgangsmaterialien, so kann der Reaktionsverlauf durch das folgende Formelschema wiedergegeben werden:If you use z. B. in process variant b) the potassium salt of N- [4-trifluoromethylpnenyl] tetrachlorophthalamic acid and zinc chloride as starting materials, the course of the reaction can be as follows Formula scheme can be reproduced:
+ ZnCI2 + ZnCI 2
CO — NH-< >—CF3 CO - NH - <> - CF 3
ZnZn
Die als Ausgangsstoff bei den erfindungsgemäß herzustellenden Verbindungen nach der Verfahrensvariante a) zu verwendete N-^-Trifluormethylphenyll-tetrachlorphthalamidsaure ist bekannt und nach literaturbekannten Verfahren herstellbar (vgl. z.B. DE-OS 29 32 689).The starting material for the compounds to be prepared according to the invention according to the process variant a) N - ^ - trifluoromethylphenyl-tetrachlorophthalamic acid to be used is known and known from the literature Process can be produced (see e.g. DE-OS 29 32 689).
Die außerdem bei der Verfahrensvariante ui einzusetzenden Hydroxide sind durch die Formel (III) definiert In dieser Formel (III) steht X für die Reste, die im Zusammenhang mit der Herstellung gegeben wurden.The hydroxides also to be used in process variant ui are defined by the formula (III) In this formula (III), X stands for the radicals which were given in connection with the preparation.
Die weiterhin bei der Verfahrensvariante b) einzusetzenden wasserlöslichen Salze der N-[4-Trifluormethylphenyl|-tetraehlorphthalaniids;iure sind durch die Formel (IV) definiert und ein Teil des Erfindungsgedankens. Sie sind neu und nach der beschriebenen Methode /. H. aus der freien Säure durch Umsetzung mit einem Alka-Ii-, Erdalkali- oder gegebenenfalls alkylsubstituierten Ammoniumhydroxid in wäßriger oder alkoholischer Lösung erhältlich.The water-soluble salts of N- [4-trifluoromethylphenyl] -tetraehlorphthalaniids; iure to be used in process variant b) are defined by the formula (IV) and are part of the inventive concept. They are new and according to the method described /. H. from the free acid by reaction with an Alka-Ii-, Alkaline earth or optionally alkyl-substituted ammonium hydroxide in aqueous or alcoholic Solution available.
Weiterhin werden bei der Verfahrensvariante b| Schwermetallsalze eingesetzt, die durch die Formel (V) definiert sind. In dieser Formel stehen M und Z für die Reste, die bereits im Zusammenhang mit der Beschreibung eier Herstellung der erfindungsgemäßen Stoffe vorzugsweise für diese Substituenten genannt wurden.Furthermore, in process variant b | Heavy metal salts used, which are defined by the formula (V) are. In this formula, M and Z stand for the radicals that are already in connection with the description A preparation of the substances according to the invention have been mentioned as preferred for these substituents.
Für die erfindungsgemäße Umsetzung nach Verfahrensvariante a) kommen als Verdünnungs- bzw. Lösungsmittel Alkohole, wie Methanol und F.thanol, und Wasser in Frage.Diluents or solvents are used for the reaction according to the invention according to process variant a) Alcohols such as methanol and F.thanol, and water in question.
Die erlindungsgemäßc Umsetzung nach Verfahrensvariante b) wird im allgemeinen in wäßrigem Medium durchgeführt.The implementation according to the invention according to process variant b) is generally carried out in an aqueous medium carried out.
Die Reaktionstemperaturen für beide Varianten a) und b) können in einem größeren Bereich variiert werden. i> Man arbeitet im allgemeinen zwischen 0 bis 500C, vorzugsweise zwischen 20 bis 400C.The reaction temperatures for both variants a) and b) can be varied over a wide range. i> One works in general between 0 to 50 0 C, preferably between 20 to 40 0 C.
Die Umsetzung erfolgt im allgemeinen bei Normaldruck.The reaction is generally carried out under normal pressure.
Bei der Durchführung der Variante a) des crfindungsgemäßcn Verfahrens setzt man die Ausgangsprodukte im allgemeinen in äquimolarcn Mengen ein. Hin Überschuß an Hydroxid schadet nicht.When carrying out variant a) of the process according to the invention, the starting products are used generally in equimolar amounts. An excess of hydroxide does no harm.
Bei der Durchführung der Variante b) des erfindungsgemäßen Verfahrens setzt man im allgemeinen die Ausgangsmaterialien in äquimolaren Verhältnissen ein.When carrying out variant b) of the process according to the invention, the starting materials are generally used in equimolar proportions.
Die Isolierung der Endprodukte bei Verfahrensvariante a) erfolgt im allgemeinen dadurch, daß man die Lösung im Vakuum zui Trockne eindampft.The end products in process variant a) are generally isolated by the Solution evaporated to dryness in vacuo.
Eine bevorzugte Ausführungsform bei der erfindungsgemäßen Verfahrensvariante b) erfolgt in der Weise, daß das wasserlösliche Salz in wäßriger oder alkoholischer Lösung aus der Säure und dem Hydroxid hergestellt w ird :? und ohne Isolierung des wasserlöslichen Salzes weitergearbeitet wird durch Zugabe einer wäßrigen Lösung des Schwermetallsalzes. Die schwerlöslichen Schwermetallsalze fallen aus, werden abgesaugt, mit Wasser gewaschen und getrocknet.A preferred embodiment in process variant b) according to the invention takes place in such a way that the water-soluble salt is produced in an aqueous or alcoholic solution from the acid and the hydroxide:? and without isolating the water-soluble salt, further work is carried out by adding an aqueous solution of the Heavy metal salt. The sparingly soluble heavy metal salts precipitate, are suctioned off and washed with water and dried.
Die erfindungsgemäßen Wirkstoffe weisen eine starke mikrobizide Wirkung auf und können zur Bekämpfung von unerwünschten Mikroorganismen praktisch eingesetzt werden. Die Wirkstoffe sind für den Gebrauch als Pflanzenschutzmittel geeignet.The active ingredients according to the invention have a strong microbicidal effect and can be used for control can be used in practice by undesirable microorganisms. The active ingredients are for use as Suitable for pesticides.
So werden z. B. bakterizide Mittel im Pflanzenschulz zur Bekämpfung von Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae und Streptomycetaceae eingesetzt.So z. B. bactericidal agents in the plant school to combat Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae are used.
Die gute Pflanzenverträglichkeit der Wirkstoffe in den zur Bekämpfung von Pflanzenkrankheiten notwendigen Konzentrationen erlaubt eine Behandlung von oberirdischen Pflanzenteilen, von Pflanz- und Saatgut, und des Bodens.The fact that the active compounds are well tolerated by plants in those necessary for combating plant diseases Concentrations allow a treatment of above-ground parts of plants, of propagation stock and seeds, and of the soil.
insbesondere sind die erfindungsgemäßen Verbindungen wirksam gegen Bakterien der Gattung Xanthorrionas, z. B. gegen Xanthomonas oryzae und Xanthomonas pelargonii; außerdem gegen Erwinia mangiferae und Corynebacterium michiganense.In particular, the compounds according to the invention are effective against bacteria of the genus Xanthorrionas, z. B. against Xanthomonas oryzae and Xanthomonas pelargonii; also against Erwinia mangiferae and Corynebacterium michiganense.
Die Wirkstoffe können in die üblichen Formulierungen übergeführt werden, wie Lösungen, Emulsionen, -to Suspensionen, Pulver, Schäume, Pasten, Granulate, Aerosole, Wirkstoff-imprägnierte Natur- und synthetische Stoffe, Feinstverkapselungen in polymeren Stoffen und in Hüllmassen für Saatgut, ferner in Formulierungen mit Brennsätzen, wie Räucherpatronen, -dosen, -Spiralen u.a., sowie ULV-KaIt- und Warmnebel-Formulierungen.The active ingredients can be converted into the usual formulations, such as solutions, emulsions, -to Suspensions, powders, foams, pastes, granulates, aerosols, active ingredient-impregnated natural and synthetic Substances, finest encapsulation in polymeric substances and in coating compounds for seeds, also in formulations with Burning sets, such as smoking cartridges, cans, spirals, etc., as well as ULV cold and warm mist formulations.
Diese Formulierungen werden in bekannter Weise hergestellt, z.B. durch Vermischen der Wirksgtoffe mit Streckmitteln, also flüssigen Lösungsmitteln, unter Druck stehenden verflüssigten Gasen und/oder festen Trä- as gerstoffen, gegebenenfalls unter Verwendung von oberflächenaktiven Mitteln, also Emulgiermitteln und/oder Dispergiermitteln und/oder schaumerzeugenden Mitteln. Im Falle der Benutzung von Wasser als Streckmittel können z. B. auch organische Lösungsmittel als Hilfslösungsmittel verwendet werden. Als flüssige Lösungsmittel kommen im wesentlichen in Frage: Aromaten, wie Xylol, Toluoi, oder Alkylnaphthaline, chlorierte Aromaten oder chlorierte aliphatische Kohlenwasserstoffe, wie Chlorbenzole, Chlorethylene oder Methylenchlo- rid, aiiphatische Kohlenwasserstoffe, wie Cyclohexan oder Paraffine, z. B. Erdölfraktionen, Alkohole, wie Butanol, oder Glykol sowie deren Ether und Ester, Ketone, wie Aceton, Methylethylketon, Methylisobutylketon oder Cyclohexanon, stark polare Lösungsmittel, wie Dimethylformamid und Dimethylsulfoxid, sowie Wasser; mit verflüssigten gasformigen Streckmitteln oder Trägerstoffen sind solche Flüssigkeiten gemeint, welche bei normaler Temperatur und unter Normaldruck gasförmig sind, z. B. Aerosol-Treibgas, wie Halogenkohlenwasserstoffe sowie Butan, Propan, Stickstoff und Kohlendioxid; als feste Trägerstoffe kommen in Frage: z. B. natürliche Gesteinsmehle, wie Kaoline, Tonerden, Talkum, Kreide, Quarz, Attapulgit, Montmorillonit oder Diatomeenerde und synthetische Gesteinsmehle, wie hochdisperse Kieselsäure, Aluminiumoxid und Silikate; als feste Trägerstoffe für Granulate kommen in Frage: z.B. gebrochene und fraktionierte natürliche Gesteine wie Calcit, Marmor, Bims, Sepiolith, Dolomit sowie synthetische Granulate aus anorganischen und organischen Mehlen sowie Granulate aus organischem Material wie Sägemehl, Kokosnußschalen, Maiskolben und Tabakstengel; als Emulgier- und/oder schaumerzeugende Mittel kommen in Frage: z. B. nichtionogene und anionische Emulgatoren, wie Polyoxyethylen-Fettsäure-Ester, Polyoxyethyien-Fettalkohol-Ether, z. B. Alkylarylpolyglykolether, Alkylsulfonate, Alkylsulfate, Arylsulfonate sowie Eiweißhydrolysate; als Dispergiermittel kommen in Frage: z. B. Lignin-Suifitabiaugen und Methyiceiiuiose.These formulations are produced in known manner, eg gerst open by mixing the Wirksgtoffe with extenders, that is liquid solvents, liquefied gases under pressure and / or solid carriers as, optionally with the use of surfactants, that is emulsifiers and / or dispersants, and / or foaming agents. In the case of the use of water as an extender, z. B. organic solvents can also be used as auxiliary solvents. The following liquid solvents are essentially: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylene or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. B. petroleum fractions, alcohols such as butanol, or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water; with liquefied gaseous extenders or carriers are meant liquids which are gaseous at normal temperature and under normal pressure, e.g. B. aerosol propellants such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide; as solid carriers come into question: z. B. natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic minerals such as highly disperse silica, aluminum oxide and silicates; Solid carriers for granules are: for example broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules made from inorganic and organic flours and granules made from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; as emulsifying and / or foam-producing agents come into question: z. B. nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. B. alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolysates; as dispersants there are: z. B. Lignin suifitabi eyes and Methyiceiiuiose.
Es können in den Formulierungen Haftmittel wie Carboxymethylcellulose, natürliche und synthetische pulverige, körnige und iatexformige Polymere verwendet werden, wie Gummiarabicum, Polyvinylalkohol, Polyvinylacetat There may be adhesives such as carboxymethyl cellulose, natural and synthetic in the formulations powdery, granular and iatexformige polymers can be used, such as gum arabic, polyvinyl alcohol, polyvinyl acetate
Es können Farbstoffe wie anorganische Pigmente, z. B. Eisenoxid, Titanoxid, Ferrocyanblau und organische Farbstoffe, wie Alizarin-, Azol- und Metallphthalocyaninfarbstoffe und Spurennährstoffe wie Salze von Eisen, Mangan, Bor, Kupfer, Koball, Molybdän und Zink verwendet werden.Dyes such as inorganic pigments, e.g. B. iron oxide, titanium oxide, ferrocyan blue and organic Dyes such as alizarin, azole and metal phthalocyanine dyes and trace nutrients such as salts of iron, Manganese, boron, copper, coball, molybdenum and zinc can be used.
Die Formulierungen enthalten im allgemeinen zwischen 0,1 und 95 Gew.-% Wirkstoff, vorzugsweise zwischen 0,5 und "0%.The formulations generally contain between 0.1 and 95% by weight of active ingredient, preferably between 0.5 and "0%.
Die erlindungsgemäßen Wirkstoffe können in den Formulierungen oder in den verschiedenen Anwendungsformen in Mischung mit anderen bekannten Wirkstoffen vorliegen, wie Fungiziden, Bakteriziden, Insektiziden, Akariziden, Nematiziden, Herbiziden, Schutzstollen gegen Vogelfraß, Wuchsstoffen, PflanzcnnährstolTen und Bodenstrukturverbesserungsmilteln.The active compounds according to the invention can be present in the formulations or in the various use forms as a mixture with other known active compounds, such as fungicides, bactericides, insecticides, Acaricides, nematicides, herbicides, protective tunnels against bird damage, growth substances, plant nutrients and Soil structure improvement agents.
Die Wirkstoffe können als solche, in Form ihrer Formulierungen oder der daraus durch weiteres Verdünnen bereiteten Anwendungsnamen, wie gebrauchsfertigen Lösungen, Emulsionen, Suspensionen, Pulver, Pasten und Granulate angewendet werden. Die Anwendung geschieht in üblicher Weise, z.B. durch Gießen, Tauchen, Spritzen, Sprühen, Vernebeln, Verdampfen, Injizieren, Verschlammen, Verstreichen, Stäuben, Streuen, Trockenbeizen, Feuchtbeizen, Naßbeizen, Schlämmbeizen oder Inkrustieren.The active ingredients can be used as such, in the form of their formulations or that obtained therefrom by further dilution Prepared application names, such as ready-to-use solutions, emulsions, suspensions, powders, pastes and granules can be used. It is used in the usual way, e.g. by pouring, dipping, Splashing, atomizing, atomizing, vaporizing, injecting, silting up, spreading, dusting, scattering, Dry pickling, wet pickling, wet pickling, slurry pickling or encrusting.
Bei der Behandlung von Pflanzenteilen können die Wirkstoffkonzentrationen in den Anwendungsformen in einem größeren Bereich variiert werden. Sie liegen im allgemeinen zwischen 1 und 0,0001 Gew.-'/»,vorzugsweise zwischen 0,5 und 0,001%.In the treatment of parts of plants, the drug concentrations in the use forms in can be varied over a larger area. They are generally between 1 and 0.0001% by weight, preferably between 0.5 and 0.001%.
Bei der Saatgutbehandlung werden im allgemeinen Wirkstoffmengen von 0,001 bis 50 g je Kilogramm Saatgut, vorzugsweise 0,01 bis 10 g, benötigt.In the treatment of seeds, amounts of active ingredient of 0.001 to 50 g per kilogram of seed are generally used, preferably 0.01 to 10 g.
Bei Behandlung des Bodens sind Wirkstoffkonzentrationen von 0,00001 bis 0,1 Gew.-%, vorzugsweise von 0,0001 bis 0,02%, am Wirkungsort erforderlich.When treating the soil, active ingredient concentrations of 0.00001 to 0.1% by weight, preferably of 0.0001 to 0.02%, required at the place of action.
Herstellungsbeispiele
Beispiel'lManufacturing examples
Example'l
4040
COOKCOOK
CONH-CONH-
148 g (0,33 Mol) N^-Trifluormethylphenylj-tetrachlorphthalamidsäure werden unter Zugabe von 100 ml Methanol in 1 Liter Wasser mit !9 g (0,33 Mo!) Kaüumhydroxid bei 20-3O0C in Lesung gebracht. Von geringen Mengen eines unlöslichen Anteils wird abfiltriert und das Filtrat im Vakuum bis zurTrockne eingedampft. Man erhält hierbei 141 g (88% derTheorie) des Kaliumsalzes von N-H-TrifluormethylphenylHetrachlorphthalamidsäure mit dem Zersetzungspunkt von 1700C.148 g (0.33 mol) of N ^ -Trifluormethylphenylj-tetrachlorphthalamidsäure be brought by the addition of 100 ml of methanol in 1 liter of water with! 9 g (0.33 Mo!) Kaüumhydroxid at 20-3O 0 C in reading. Small amounts of an insoluble fraction are filtered off and the filtrate is evaporated to dryness in vacuo. Here, 141 g (88% derTheorie) is obtained the potassium salt of NH-TrifluormethylphenylHetrachlorphthalamidsäure with the decomposition point of 170 0 C.
4545
COO-COO-
CONH-CONH-
MgMg
5555 6060 6565
135 g (0,3 MoI) N-(4-TrinuormethyIphenyl)-tetrachlorphthalamidsäure werden unter Zusatz von 100 ml Methanol in 1 Liter Wasser mit 12 g (0,3 Mol) Ätznatron in Lösung gebracht. Anschließend tropft man bei 20-250C eine Lösung von 40 g (0,2 Mol) Magnesiumchloridhexahydrat in 200 ml Wasser zu. Das ausgefallene Magnesiumsalz wird abgesaugt, mit Wasser gewaschen und getrocknet. Man erhält 115 g (84% der Theorie) des Magnesiumsalzes von N-(4-Trifluormethylphenyl)-tetrachlorphthalarnidsäure mit einem Schmelzpunkt > 3000C.135 g (0.3 mol) of N- (4-TrinuormethyIphenyl) tetrachlorophthalamic acid are brought into solution with the addition of 100 ml of methanol in 1 liter of water with 12 g (0.3 mol) of caustic soda. Then added dropwise a solution of 40 g (0.2 mol) of magnesium in 200 ml of water at 20-25 0 C. The precipitated magnesium salt is filtered off with suction, washed with water and dried. This gives 115 g (84% of theory) of the magnesium salt of N- (4-trifluoromethylphenyl) -tetrachlorphthalarnidsäure having a melting point> 300 0 C.
In analoger Weise erhält man folgende Salze der Formel (I)The following salts of the formula (I) are obtained in an analogous manner
COOMCOOM
CO-CO-
Nr.No.
Analyse des Metall;, Berechnet GefundenAnalysis of the metal; Calculated Found
VerwendungsbeispieleUsage examples
Im nachfolgenden Beispiel wird die nachstehende aufgeführte bekannte Verbindung als Vergleichssubstanz eingesetzt:In the following example, the known compound listed below is used as a comparison substance used:
CO-OHCO-OH
Beispiel AgarplattentestExample agar plate test
Verwendeter NährbodenUsed medium
15 Gew.-Teile 10 Gew.-Teile 8 Gew.-Teile 4 Gew.-Teile 2 Gew.-Teile 0,3 Gew.-Teile15 parts by weight 10 parts by weight 8 parts by weight 4 parts by weight 2 parts by weight 0.3 parts by weight
Agar-AgarAgar Agar
SaccharoseSucrose
CaseinhydrolysatCasein hydrolyzate
HefeextraktYeast extract
DikaliumhydrogenphosphatDipotassium hydrogen phosphate
MagnesiumsulfatMagnesium sulfate
werden in 1000 ml destilliertem Wasser gelöst und 30 Minuten bei 1210C autoklaviert.are dissolved in 1000 ml of distilled water and autoclaved at 121 ° C. for 30 minutes.
Lösungsmittel: 40 Gew.-Teile Aceton.Solvent: 40 parts by weight of acetone.
Mengenverhältnis von Lösungsmittel zu Nährboden: 2 : 100.Amount ratio of solvent to culture medium: 2: 100.
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man I Gew.-Teil Wirkstoff mit der angegebenen Menge Lösungsmittel.To produce an appropriate preparation of active ingredient, I part by weight of active ingredient is mixed with the specified Amount of solvent.
Das Konzentrat wird im genannten Mengenverhältnis mit dem flüssigen Nährboden gründlich vermischt und 45 in Petrischalen gegossen.The concentrate is thoroughly mixed with the liquid nutrient medium in the specified proportions and 45 poured into petri dishes.
Ist der Nährboden erkaltet und fest, werden die Platten mit folgenden Mikroorganismen beimpft und bei ca. 210C inkubiert:If the culture medium has cooled down and is solid, the plates are inoculated with the following microorganisms and incubated at approx. 21 ° C:
Erwinia mangiferae soErwinia mangiferae like that
Xanthomonas oryzae Xanthomooas pelargonü Corynebacterium michiganenseXanthomonas oryzae Xanthomooas pelargonü Corynebacterium michiganense
Die Auswertung erfolgt je nach Wachstumsgeschwindigkeit der Mikroorganismen nach 2 bis 8 Tagen, wobei 55 die Wachstumshemmung als Maß fur die Wirkung der Präparate herangezogen wird.The evaluation takes place depending on the growth rate of the microorganisms after 2 to 8 days, with 55 the growth inhibition is used as a measure of the effect of the preparations.
Eine Überlegenheit gegenüber dem Stand der Technik zeigen in diesem Test die Verbindungen gemäß folgenden Herstellungsbeispielen: 3, 4 und 5.In this test, the compounds according to the following show a superiority over the prior art Production examples: 3, 4 and 5.
Claims (7)
1. Salze der N-(4-Tritluormethylphenyl)-tetrachlorphthalamidsäure der Formel (I)Patent claims:
1. Salts of N- (4-tritluoromethylphenyl) tetrachlorophthalamic acid of the formula (I)
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE3220883A DE3220883C2 (en) | 1982-06-03 | 1982-06-03 | Salts of N- (4-trifluoromethylphenyl) tetrachlorophthalamic acid, process for their preparation and their use as pesticides |
JP58095140A JPS58219153A (en) | 1982-06-03 | 1983-05-31 | Salts of n-(4-trifluoromethylphenyl)- tetrachlorophthalamic acid, manufacture and insecticide |
PH28994A PH20345A (en) | 1982-06-03 | 1983-06-01 | Salts of n-(4-trifluoromethylphenyl)-tetrachlorophthalamic acid, their composition and their use |
KR1019830002476A KR840005085A (en) | 1982-06-03 | 1983-06-02 | Process for preparing salts of N- (4-trifluoromethylphenyl) -tetrachlorophthalamic acid |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE3220883A DE3220883C2 (en) | 1982-06-03 | 1982-06-03 | Salts of N- (4-trifluoromethylphenyl) tetrachlorophthalamic acid, process for their preparation and their use as pesticides |
Publications (2)
Publication Number | Publication Date |
---|---|
DE3220883A1 DE3220883A1 (en) | 1983-12-08 |
DE3220883C2 true DE3220883C2 (en) | 1985-11-14 |
Family
ID=6165187
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE3220883A Expired DE3220883C2 (en) | 1982-06-03 | 1982-06-03 | Salts of N- (4-trifluoromethylphenyl) tetrachlorophthalamic acid, process for their preparation and their use as pesticides |
Country Status (4)
Country | Link |
---|---|
JP (1) | JPS58219153A (en) |
KR (1) | KR840005085A (en) |
DE (1) | DE3220883C2 (en) |
PH (1) | PH20345A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8859620B2 (en) | 2009-08-31 | 2014-10-14 | University Of Notre Dame Du Lac | Phthalanilate compounds and methods of use |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4826213B1 (en) * | 1970-09-11 | 1973-08-07 | ||
JPS5720924B2 (en) * | 1974-02-20 | 1982-05-04 | ||
DE2932689A1 (en) * | 1979-08-11 | 1981-02-26 | Bayer Ag | TETRACHLORPHTHALAMID ACIDS, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE OF BACTERICIDES |
DE3025220A1 (en) * | 1980-07-03 | 1982-02-04 | Bayer Ag, 5090 Leverkusen | TETRACHLORPHTHALAMID ACID DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE OF BACTERICIDES |
-
1982
- 1982-06-03 DE DE3220883A patent/DE3220883C2/en not_active Expired
-
1983
- 1983-05-31 JP JP58095140A patent/JPS58219153A/en active Granted
- 1983-06-01 PH PH28994A patent/PH20345A/en unknown
- 1983-06-02 KR KR1019830002476A patent/KR840005085A/en not_active Application Discontinuation
Non-Patent Citations (1)
Title |
---|
NICHTS-ERMITTELT |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8859620B2 (en) | 2009-08-31 | 2014-10-14 | University Of Notre Dame Du Lac | Phthalanilate compounds and methods of use |
Also Published As
Publication number | Publication date |
---|---|
JPS6241705B2 (en) | 1987-09-04 |
PH20345A (en) | 1986-12-04 |
JPS58219153A (en) | 1983-12-20 |
KR840005085A (en) | 1984-11-03 |
DE3220883A1 (en) | 1983-12-08 |
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