SK219587A3 - Agent for plants growth control - Google Patents

Agent for plants growth control Download PDF

Info

Publication number: SK219587A3
Authority: SK; Slovakia
Prior art keywords: compound; plant growth; etphone; growth regulating; malonic acid
Prior art date: 1986-03-31

Application number

SK2195-87A

Other languages

English (en)

Slovak (sk)

Other versions

SK278455B6 (en

Inventor

Raymond Michael See

Charles David Fritz

David Treadway Manning

Thomas Neil Wheeler

Anson Richard Cooke

Original Assignee

Rhone Poulenc Bv

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.)

1986-03-31

Filing date

1987-03-30

Publication date

1997-06-04

1987-03-04 Priority claimed from US07/017,150 external-priority patent/US5123951A/en

1987-03-30 Application filed by Rhone Poulenc Bv filed Critical Rhone Poulenc Bv

1997-06-04 Publication of SK219587A3 publication Critical patent/SK219587A3/sk

1997-06-04 Publication of SK278455B6 publication Critical patent/SK278455B6/sk

Links

230000012010 growth Effects 0.000 title description 27
239000000203 mixture Substances 0.000 claims abstract description 187
230000008635 plant growth Effects 0.000 claims abstract description 85
230000001105 regulatory effect Effects 0.000 claims abstract description 73
150000002690 malonic acid derivatives Chemical class 0.000 claims description 56
UDPGUMQDCGORJQ-UHFFFAOYSA-N (2-chloroethyl)phosphonic acid Chemical compound OP(O)(=O)CCCl UDPGUMQDCGORJQ-UHFFFAOYSA-N 0.000 claims description 55
229910052739 hydrogen Inorganic materials 0.000 claims description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
150000003839 salts Chemical class 0.000 claims description 10
230000001276 controlling effect Effects 0.000 claims description 7
229910052799 carbon Inorganic materials 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 5
150000003863 ammonium salts Chemical class 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims description 2
150000001447 alkali salts Chemical class 0.000 claims description 2
125000005210 alkyl ammonium group Chemical group 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
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-1 malonic acid derivative compound Chemical class 0.000 abstract description 27
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PCHYYOCUCGCSBU-UHFFFAOYSA-N 4-bromo-2-methylaniline Chemical compound CC1=CC(Br)=CC=C1N PCHYYOCUCGCSBU-UHFFFAOYSA-N 0.000 description 5
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CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
240000005979 Hordeum vulgare Species 0.000 description 4
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WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
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VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
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MEDTZWPBIYWHBW-UHFFFAOYSA-N diethyl cycloprop-2-ene-1,1-dicarboxylate Chemical compound CCOC(=O)C1(C(=O)OCC)C=C1 MEDTZWPBIYWHBW-UHFFFAOYSA-N 0.000 description 3
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CAFVGIPKHPBMJS-UHFFFAOYSA-N dimethyl 2,2-dimethylpropanedioate Chemical compound COC(=O)C(C)(C)C(=O)OC CAFVGIPKHPBMJS-UHFFFAOYSA-N 0.000 description 1
OREAFAJWWJHCOT-UHFFFAOYSA-N dimethylmalonic acid Chemical compound OC(=O)C(C)(C)C(O)=O OREAFAJWWJHCOT-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
UUUXEDQEPAEVEZ-UHFFFAOYSA-N ethyl 1-[(3,5-dichlorophenyl)carbamoyl]cyclobutane-1-carboxylate Chemical compound C=1C(Cl)=CC(Cl)=CC=1NC(=O)C1(C(=O)OCC)CCC1 UUUXEDQEPAEVEZ-UHFFFAOYSA-N 0.000 description 1
NAERMZUIUQCKNK-UHFFFAOYSA-N ethyl 1-carbonochloridoylcyclobutane-1-carboxylate Chemical compound CCOC(=O)C1(C(Cl)=O)CCC1 NAERMZUIUQCKNK-UHFFFAOYSA-N 0.000 description 1
DBJKGNRHRBGJJZ-UHFFFAOYSA-N ethyl 2-[(4-bromo-2-methylphenyl)carbamoyl]-3-methylbut-2-enoate Chemical compound CCOC(=O)C(=C(C)C)C(=O)NC1=CC=C(Br)C=C1C DBJKGNRHRBGJJZ-UHFFFAOYSA-N 0.000 description 1
INDHBSCZARCFDW-UHFFFAOYSA-N ethyl 2-[(4-bromo-2-methylphenyl)carbamoyl]butanoate Chemical compound CCOC(=O)C(CC)C(=O)NC1=CC=C(Br)C=C1C INDHBSCZARCFDW-UHFFFAOYSA-N 0.000 description 1
NGDNCOUQYWVQLS-UHFFFAOYSA-N ethyl 2-carbonochloridoylbutanoate Chemical compound CCOC(=O)C(CC)C(Cl)=O NGDNCOUQYWVQLS-UHFFFAOYSA-N 0.000 description 1
VNGQBYRCHLYDPJ-UHFFFAOYSA-N ethyl 3-(4-bromo-2-methylanilino)-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)NC1=CC=C(Br)C=C1C VNGQBYRCHLYDPJ-UHFFFAOYSA-N 0.000 description 1
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000003925 fat Substances 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
210000003754 fetus Anatomy 0.000 description 1
230000000855 fungicidal effect Effects 0.000 description 1
230000035784 germination Effects 0.000 description 1
IXORZMNAPKEEDV-UHFFFAOYSA-N gibberellic acid GA3 Natural products OC(=O)C1C2(C3)CC(=C)C3(O)CCC2C2(C=CC3O)C1C3(C)C(=O)O2 IXORZMNAPKEEDV-UHFFFAOYSA-N 0.000 description 1
IXORZMNAPKEEDV-OBDJNFEBSA-N gibberellin A3 Chemical compound C([C@@]1(O)C(=C)C[C@@]2(C1)[C@H]1C(O)=O)C[C@H]2[C@]2(C=C[C@@H]3O)[C@H]1[C@]3(C)C(=O)O2 IXORZMNAPKEEDV-OBDJNFEBSA-N 0.000 description 1
235000002532 grape seed extract Nutrition 0.000 description 1
230000009036 growth inhibition Effects 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
238000003306 harvesting Methods 0.000 description 1
230000012447 hatching Effects 0.000 description 1
235000008216 herbs Nutrition 0.000 description 1
239000005556 hormone Substances 0.000 description 1
229940088597 hormone Drugs 0.000 description 1
SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
230000000749 insecticidal effect Effects 0.000 description 1
229940039717 lanolin Drugs 0.000 description 1
235000019388 lanolin Nutrition 0.000 description 1
239000012263 liquid product Substances 0.000 description 1
238000000622 liquid--liquid extraction Methods 0.000 description 1
235000009973 maize Nutrition 0.000 description 1
IQBWTCHGQZRPPP-UHFFFAOYSA-N methyl 3-(3,5-dichloroanilino)-2-methoxy-3-oxopropanoate Chemical compound COC(=O)C(OC)C(=O)NC1=CC(Cl)=CC(Cl)=C1 IQBWTCHGQZRPPP-UHFFFAOYSA-N 0.000 description 1
FNMLUIQLNJKWSQ-UHFFFAOYSA-N methyl 3-chloro-2-methoxy-3-oxopropanoate Chemical compound COC(C(Cl)=O)C(=O)OC FNMLUIQLNJKWSQ-UHFFFAOYSA-N 0.000 description 1
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
230000003129 miticidal effect Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
230000001069 nematicidal effect Effects 0.000 description 1
229960002715 nicotine Drugs 0.000 description 1
SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
231100001184 nonphytotoxic Toxicity 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
239000008188 pellet Substances 0.000 description 1
238000003359 percent control normalization Methods 0.000 description 1
239000003209 petroleum derivative Substances 0.000 description 1
235000009048 phenolic acids Nutrition 0.000 description 1
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
231100000208 phytotoxic Toxicity 0.000 description 1
238000005554 pickling Methods 0.000 description 1
244000000003 plant pathogen Species 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004033 plastic Substances 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
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000011698 potassium fluoride Substances 0.000 description 1
235000003270 potassium fluoride Nutrition 0.000 description 1
235000012015 potatoes Nutrition 0.000 description 1
230000002265 prevention Effects 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
239000003380 propellant Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000001850 reproductive effect Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
238000010092 rubber production Methods 0.000 description 1
230000007226 seed germination Effects 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
238000007711 solidification Methods 0.000 description 1
230000008023 solidification Effects 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
241000894007 species Species 0.000 description 1
238000002798 spectrophotometry method Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
230000001629 suppression Effects 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000005737 synergistic response Effects 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
238000011179 visual inspection Methods 0.000 description 1
235000020234 walnut Nutrition 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
239000008096 xylene 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
- A01N37/18—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
- 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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals

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)
Pyridine Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Cultivation Of Plants (AREA)
Breeding Of Plants And Reproduction By Means Of Culturing (AREA)

SK2195-87A 1986-03-31 1987-03-30 Agent for growth regulation of plants SK278455B6 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US84639286A	1986-03-31	1986-03-31
US07/017,150 US5123951A (en)	1986-03-31	1987-03-04	Synergistic plant growth regulator compositions

Publications (2)

Publication Number	Publication Date
SK219587A3 true SK219587A3 (en)	1997-06-04
SK278455B6 SK278455B6 (en)	1997-06-04

Family

ID=26689524

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK2195-87A SK278455B6 (en)	1986-03-31	1987-03-30	Agent for growth regulation of plants

Country Status (15)

Country	Link
EP (1)	EP0262209B1 (da)
JP (1)	JP2749578B2 (da)
CN (1)	CN1024544C (da)
AU (1)	AU614488B2 (da)
CA (1)	CA1291343C (da)
DK (1)	DK175682B1 (da)
FI (1)	FI90189C (da)
HK (1)	HK80294A (da)
HU (1)	HU201455B (da)
IL (1)	IL82054A (da)
NO (1)	NO176041C (da)
OA (1)	OA08507A (da)
PT (1)	PT84596B (da)
SK (1)	SK278455B6 (da)
WO (1)	WO1987005781A2 (da)

Families Citing this family (35)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU7284387A (en) *	1986-03-31	1987-10-20	Union Carbide Agricultural Products Company Inc.	Use of malonic acid derivative compounds for increasing crop yield
WO1987005898A2 (en) *	1986-03-31	1987-10-08	Rhone-Poulenc Nederlands B.V.	Use of malonic acid derivative compounds for retarding plant growth
JP2673211B2 (ja) *	1988-05-19	1997-11-05	クミアイ化学工業株式会社	植物生長調節組成物
FR2700242B1 (fr) *	1993-01-12	1995-03-24	Rhone Poulenc Agrochimie	Mélange régulateur de croissance des plantes.
US5478796A (en) *	1994-03-04	1995-12-26	Rhone-Poulenc Agrochimie	Plant growth regulatory mixture comprising mepiquat and cyclanilide or other cyclopropylmalonic acid anilides
US6355838B1 (en)	1999-02-02	2002-03-12	National Starch And Chemical Investment Holding Corporation	Reagents for heat activated polymer crosslinking
DE50000541D1 (de)	1999-03-03	2002-10-31	Basf Ag	Diureide und deren Verwendung
DE60041786D1 (de) *	2000-07-14	2009-04-23	Nat Starch Chem Invest	Reagenz zum wärmeaktivierten vernetzen von polymeren
US7507767B2 (en)	2001-02-08	2009-03-24	Schering Corporation	Cannabinoid receptor ligands
US7067539B2 (en)	2001-02-08	2006-06-27	Schering Corporation	Cannabinoid receptor ligands
WO2008150487A2 (en) *	2007-05-31	2008-12-11	Texas Tech University	Synthesis of half esters
KR20130016041A (ko) *	2011-08-04	2013-02-14	재단법인 의약바이오컨버젼스연구단	신규한 아닐린 유도체 및 이의 용도
RU2548495C1 (ru) *	2014-03-03	2015-04-20	Михаил Аркадьевич Ершов	Способ стимуляции всхожести семян зерновых культур
CA2949793C (en)	2014-06-19	2024-02-27	Ariad Pharmaceuticals, Inc.	Heteroaryl compounds for kinase inhibition
RU2564165C1 (ru) *	2014-08-12	2015-09-27	Михаил Аркадьевич Ершов	Способ получения стимулятора зерновых культур
RU2566029C1 (ru) *	2014-08-19	2015-10-20	Михаил Аркадьевич Ершов	Стимулятор для предпосевной обработки семян зерновых культур
RU2564206C1 (ru) *	2014-08-20	2015-09-27	Михаил Аркадьевич Ершов	Способ стимуляции всхожести семян зерновых культур
RU2565883C1 (ru) *	2014-08-20	2015-10-20	Михаил Аркадьевич Ершов	Способ получения стимулятора зерновых культур
CN107879946A (zh) *	2017-04-25	2018-04-06	湖南比德生化科技股份有限公司	一种制备环丙酰胺酸的方法
WO2019222093A1 (en)	2018-05-14	2019-11-21	Ariad Pharmaceuticals, Inc.	Pharmaceutical salts of pyrimidine derivatives and method of treating disorders
CN109329307A (zh) *	2018-10-19	2019-02-15	安徽省天下彩源种苗科技有限公司	一种提高芽接成活率的处理剂
EP4110763B8 (en) *	2020-02-28	2026-08-05	BASF Agricultural Solutions Deutschland GmbH	Herbicidal malonamides
AR125237A1 (es) *	2021-03-30	2023-06-28	Valent Biosciences Llc	Inhibidores de succinato deshidrogenasa para interrumpir la latencia
CN116135020A (zh) *	2021-11-16	2023-05-19	郑州尼采生物科技有限公司	一种新型植物生长调节剂的剂型组合物
WO2025209874A1 (en) *	2024-04-05	2025-10-09	Basf Se	Herbicide compositions comprising a malonamide compound and a cellulose biosynthesis inhibitor for effective weed control.
WO2025209868A1 (en) *	2024-04-05	2025-10-09	Basf Se	Herbicide compositions comprising a malonamide compound and an auxin mimic for effective weed control.
WO2025209871A1 (en) *	2024-04-05	2025-10-09	Basf Se	Herbicide compositions comprising a malonamide compound and a mitosis inhibitor for effective weed control
WO2025209879A1 (en) *	2024-04-05	2025-10-09	Basf Se	Herbicide compositions comprising a malonamide compound and an acetolactate synthase inhibitor for effective weed control.
WO2025209881A1 (en) *	2024-04-05	2025-10-09	Basf Se	Herbicide compositions comprising a malonamide compound and a lipid biosynthesis inhibitor for effective weed control
WO2025209880A1 (en) *	2024-04-05	2025-10-09	Basf Se	Herbicide compositions comprising a malonamide compound and a photosynthesis inhibitor for effective weed control.
WO2025209862A1 (en) *	2024-04-05	2025-10-09	Basf Se	Herbicide compositions comprising a malonamide compound and a further herbicide for effective weed control.
WO2025209870A1 (en) *	2024-04-05	2025-10-09	Basf Se	Herbicide compositions comprising a malonamide compound and a very long-chain fatty acid synthesis inhibitor for effective weed control
WO2026154047A1 (en) *	2025-01-15	2026-07-23	Basf Agricultural Solutions Deutschland Gmbh	Herbicide compositions comprising a malonamide compound and at least two further herbicides for effective weed control
WO2026154048A1 (en) *	2025-01-15	2026-07-23	Basf Agricultural Solutions Deutschland Gmbh	Herbicide compositions comprising a malonamide compound and at least two further herbicides for effective weed control
WO2026154046A1 (en) *	2025-01-15	2026-07-23	Basf Agricultural Solutions Deutschland Gmbh	Herbicide compositions comprising a malonamide compound and at least two further herbicides for effective weed control

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3072473A (en) *	1959-10-07	1963-01-08	Us Rubber Co	Plant growth regulants
US4374661A (en)	1967-12-27	1983-02-22	Union Carbide Corporation	Growth regulation process
US3879188A (en)	1969-10-24	1975-04-22	Amchem Prod	Growth regulation process
US4401454A (en)	1969-10-24	1983-08-30	Union Carbide Corporation	Growth regulation methods
SU512691A3 (ru)	1971-03-06	1976-04-30	Байер Аг (Фирма)	Регул тор роста растений
US4240819A (en)	1972-01-28	1980-12-23	Union Carbide Agricultural Products, Inc.	Method for the inhibition of plant growth
US3927062A (en)	1972-05-15	1975-12-16	Shell Oil Co	Plant growth regulators
AU502582B2 (en) *	1975-04-18	1979-08-02	Union Carbide Agricultural Products Company Inc.	Method of growth regulation and compositions
HU179142B (en) *	1977-09-28	1982-08-28	Chinoin Gyogyszer Es Vegyeszet	Process for improving defoliation and cutting fruits with treating plants withsynergistic composition of plant-ascission-improving activity,containing two active agents
US4359334A (en)	1980-04-28	1982-11-16	Gaf Corporation	Composition for plant growth regulation
US4332612A (en)	1980-07-02	1982-06-01	Gaf Corporation	Plant growth promoting composition
US4352869A (en)	1980-12-24	1982-10-05	Union Carbide Corporation	Solid state electrolytes
JPS5939803A (ja)	1982-08-27	1984-03-05	Nissan Chem Ind Ltd	植物生長調節剤
WO1987005898A2 (en) *	1986-03-31	1987-10-08	Rhone-Poulenc Nederlands B.V.	Use of malonic acid derivative compounds for retarding plant growth
AU7284387A (en) *	1986-03-31	1987-10-20	Union Carbide Agricultural Products Company Inc.	Use of malonic acid derivative compounds for increasing crop yield

1987
- 1987-03-30 CN CN87103565A patent/CN1024544C/zh not_active Expired - Lifetime
- 1987-03-30 AU AU72371/87A patent/AU614488B2/en not_active Expired
- 1987-03-30 IL IL82054A patent/IL82054A/xx not_active IP Right Cessation
- 1987-03-30 HU HU872058A patent/HU201455B/hu unknown
- 1987-03-30 SK SK2195-87A patent/SK278455B6/sk unknown
- 1987-03-30 JP JP62502284A patent/JP2749578B2/ja not_active Expired - Lifetime
- 1987-03-30 CA CA000533366A patent/CA1291343C/en not_active Expired - Lifetime
- 1987-03-30 WO PCT/US1987/000648 patent/WO1987005781A2/en not_active Ceased
- 1987-03-30 EP EP87902947A patent/EP0262209B1/en not_active Expired - Lifetime
- 1987-03-31 PT PT84596A patent/PT84596B/pt unknown
- 1987-03-31 OA OA59096A patent/OA08507A/xx unknown
- 1987-11-26 NO NO874929A patent/NO176041C/no unknown
- 1987-11-27 DK DK198706235A patent/DK175682B1/da not_active IP Right Cessation
- 1987-11-30 FI FI875279A patent/FI90189C/fi not_active IP Right Cessation
1994
- 1994-08-11 HK HK80294A patent/HK80294A/en not_active IP Right Cessation

Also Published As

Publication number	Publication date
JPS63503064A (ja)	1988-11-10
FI90189B (fi)	1993-09-30
CA1291343C (en)	1991-10-29
NO874929D0 (no)	1987-11-26
HK80294A (en)	1994-08-19
DK175682B1 (da)	2005-01-17
WO1987005781A2 (en)	1987-10-08
IL82054A (en)	1992-11-15
HU201455B (en)	1990-11-28
AU7237187A (en)	1987-10-20
HUT46519A (en)	1988-11-28
AU614488B2 (en)	1991-09-05
JP2749578B2 (ja)	1998-05-13
WO1987005781A3 (en)	1987-12-03
CN1024544C (zh)	1994-05-18
CN87103565A (zh)	1988-03-02
NO874929L (no)	1988-01-19
FI875279A0 (fi)	1987-11-30
FI875279L (fi)	1987-11-30
DK623587D0 (da)	1987-11-27
SK278455B6 (en)	1997-06-04
PT84596A (en)	1987-04-01
FI90189C (fi)	1994-01-10
EP0262209A1 (en)	1988-04-06
DK623587A (da)	1988-01-26
OA08507A (fr)	1988-07-29
PT84596B (pt)	1989-11-30
IL82054A0 (en)	1987-10-20
EP0262209B1 (en)	1992-08-05
NO176041C (no)	1995-01-25
NO176041B (no)	1994-10-17

Publication	Publication Date	Title
CZ280917B6 (cs)	1996-05-15	Prostředek pro regulaci růstu rostlin
SK278455B6 (en)	1997-06-04	Agent for growth regulation of plants
JP2693774B2 (ja)	1997-12-24	マロン酸誘導体化合物の植物の成長を抑制するための使用
EP0261226A1 (en)	1988-03-30	Use of malonic acid derivative compounds for increasing crop yield
EP0065712B1 (de)	1987-07-22	N-(1-Alkenyl)-chloressigsäureanilide, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren
RU2088571C1 (ru)	1997-08-27	Производные малоновой кислоты
DE3780897T2 (de)	1993-05-06	Synergitische pflanzenwachstums-regulatorzusammensetzungen
RU2088085C1 (ru)	1997-08-27	Композиция для дефолиации растений и способ дефолиации растений
KR800001571B1 (ko)	1980-12-28	옥사졸리딘 및 티아졸리딘 제초제 해독조성물
JPS6115065B2 (da)	1986-04-22
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NO874928L (no)	1988-01-29	Anvendelse av malonsyrederivatforbindelser for aa gi oekende avlinger.
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JPS5869804A (ja)	1983-04-26	植物生長調整剤
JPS5877865A (ja)	1983-05-11	新規ピラゾ−ル誘導体
JPS62174063A (ja)	1987-07-30	トリアゾ−ル誘導体およびそれを有効成分とする植物生長調節剤ならびに農園芸用殺菌剤
JPS6320427B2 (da)	1988-04-27