CA1120747A - Herbicides - Google Patents

Herbicides

Info

Publication number: CA1120747A
Authority: CA; Canada
Prior art keywords: amino; propyl; acid; carboxy; methylphosphinic acid
Prior art date: 1976-05-17
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000360330A

Other languages

English (en)

Inventor

Walter Rupp

Manfred Finke

Hermann Bieringer

Peter Langeluddeke

Hans-Jerg Kleiner

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

Hoechst AG

Original Assignee

Hoechst AG

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1976-05-17

Filing date

1980-09-16

Publication date

1982-03-30

1977-05-16 Priority claimed from CA000278456A external-priority patent/CA1120052A/fr

1980-09-16 Application filed by Hoechst AG filed Critical Hoechst AG

1980-09-16 Priority to CA000360330A priority Critical patent/CA1120747A/fr

1982-03-30 Application granted granted Critical

1982-03-30 Publication of CA1120747A publication Critical patent/CA1120747A/fr

Status Expired legal-status Critical Current

Links

239000004009 herbicide Substances 0.000 title description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 23
238000000034 method Methods 0.000 claims description 7
230000008635 plant growth Effects 0.000 claims description 4
241000196324 Embryophyta Species 0.000 abstract description 21
150000001875 compounds Chemical class 0.000 abstract description 13
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
239000000243 solution Substances 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 10
229910000041 hydrogen chloride Inorganic materials 0.000 description 10
239000002253 acid Substances 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
239000013543 active substance Substances 0.000 description 6
239000000155 melt Substances 0.000 description 6
239000000126 substance Substances 0.000 description 6
238000011156 evaluation Methods 0.000 description 5
239000001257 hydrogen Substances 0.000 description 5
229910052739 hydrogen Inorganic materials 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
239000000843 powder Substances 0.000 description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
159000000000 sodium salts Chemical class 0.000 description 4
239000002904 solvent Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
244000038559 crop plants Species 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
230000002363 herbicidal effect Effects 0.000 description 3
239000000047 product Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
238000003756 stirring Methods 0.000 description 3
OGNVQLDIPUXYDH-ZPKKHLQPSA-N (2R,3R,4S)-3-(2-methylpropanoylamino)-4-(4-phenyltriazol-1-yl)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid Chemical compound CC(C)C(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)OC(C(O)=O)=C[C@@H]1N1N=NC(C=2C=CC=CC=2)=C1 OGNVQLDIPUXYDH-ZPKKHLQPSA-N 0.000 description 2
KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 2
GXJQMKFJQFGQKV-KHPPLWFESA-N 2-[methyl-[(z)-octadec-9-enoyl]amino]ethanesulfonic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)N(C)CCS(O)(=O)=O GXJQMKFJQFGQKV-KHPPLWFESA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
125000000217 alkyl group Polymers 0.000 description 2
150000003931 anilides Chemical class 0.000 description 2
FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
150000001879 copper Chemical class 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
239000004495 emulsifiable concentrate Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
239000007789 gas Substances 0.000 description 2
238000003306 harvesting Methods 0.000 description 2
229940091173 hydantoin Drugs 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
239000013067 intermediate product Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
239000000203 mixture Substances 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
238000010992 reflux Methods 0.000 description 2
238000007127 saponification reaction Methods 0.000 description 2
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
239000007921 spray Substances 0.000 description 2
-1 stearyl amines Chemical class 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
SKDCPWHZRBODIM-UHFFFAOYSA-N 1-[ethenyl(methyl)phosphoryl]oxyethane Chemical compound CCOP(C)(=O)C=C SKDCPWHZRBODIM-UHFFFAOYSA-N 0.000 description 1
LGFOUFJSDLMHFJ-UHFFFAOYSA-N 2-acetyl-2-aminopropanedioic acid Chemical class CC(=O)C(N)(C(O)=O)C(O)=O LGFOUFJSDLMHFJ-UHFFFAOYSA-N 0.000 description 1
IDBRULKICVRMNG-UHFFFAOYSA-N 2-amino-4-hydroxyphosphonoylbutanoic acid Chemical compound OC(=O)C(N)CCP(O)=O IDBRULKICVRMNG-UHFFFAOYSA-N 0.000 description 1
ZNVFLMYQLVSXSK-UHFFFAOYSA-N 4-[butoxy(methyl)phosphoryl]butan-2-one Chemical compound CCCCOP(C)(=O)CCC(C)=O ZNVFLMYQLVSXSK-UHFFFAOYSA-N 0.000 description 1
244000291564 Allium cepa Species 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
235000005781 Avena Nutrition 0.000 description 1
244000075850 Avena orientalis Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
235000007516 Chrysanthemum Nutrition 0.000 description 1
240000005250 Chrysanthemum indicum Species 0.000 description 1
244000192528 Chrysanthemum parthenium Species 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
244000052363 Cynodon dactylon Species 0.000 description 1
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
241000192043 Echinochloa Species 0.000 description 1
241000508725 Elymus repens Species 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
241000257303 Hymenoptera Species 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
241000209082 Lolium Species 0.000 description 1
235000017945 Matricaria Nutrition 0.000 description 1
235000007232 Matricaria chamomilla Nutrition 0.000 description 1
HOKDBMAJZXIPGC-UHFFFAOYSA-N Mequitazine Chemical compound C12=CC=CC=C2SC2=CC=CC=C2N1CC1C(CC2)CCN2C1 HOKDBMAJZXIPGC-UHFFFAOYSA-N 0.000 description 1
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
102400000830 Saposin-B Human genes 0.000 description 1
101800001697 Saposin-B Proteins 0.000 description 1
235000005775 Setaria Nutrition 0.000 description 1
241000232088 Setaria <nematode> Species 0.000 description 1
241000220261 Sinapis Species 0.000 description 1
244000061456 Solanum tuberosum Species 0.000 description 1
235000002595 Solanum tuberosum Nutrition 0.000 description 1
125000005037 alkyl phenyl group Chemical group 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
230000000332 continued effect Effects 0.000 description 1
239000010949 copper Substances 0.000 description 1
230000000254 damaging effect Effects 0.000 description 1
ISOLMABRZPQKOV-UHFFFAOYSA-N diethyl 2-acetamidopropanedioate Chemical compound CCOC(=O)C(NC(C)=O)C(=O)OCC ISOLMABRZPQKOV-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
210000005069 ears Anatomy 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
MQIGTIFMSSGUBS-UHFFFAOYSA-N ethenylphosphinic acid Chemical class OP(=O)C=C MQIGTIFMSSGUBS-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
241001233957 eudicotyledons Species 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
238000000227 grinding Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 1
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
229910000069 nitrogen hydride Inorganic materials 0.000 description 1
238000010534 nucleophilic substitution reaction Methods 0.000 description 1
125000001117 oleyl group Polymers [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
150000002989 phenols Chemical class 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
235000012015 potatoes Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
239000003380 propellant Substances 0.000 description 1
239000010453 quartz Substances 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
230000036647 reaction Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Inorganic materials [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 1
238000009331 sowing Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1
238000009736 wetting Methods 0.000 description 1

Landscapes

Agricultural Chemicals And Associated Chemicals (AREA)

CA000360330A 1976-05-17 1980-09-16 Herbicides Expired CA1120747A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000360330A CA1120747A (fr)	1976-05-17	1980-09-16	Herbicides

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
CH6153/76		1976-05-17
CH615376		1976-05-17
CA000278456A CA1120052A (fr)	1976-05-17	1977-05-16	Derives de l'acide phosphinique
CA000360330A CA1120747A (fr)	1976-05-17	1980-09-16	Herbicides

Publications (1)

Publication Number	Publication Date
CA1120747A true CA1120747A (fr)	1982-03-30

Family

ID=27165077

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000360330A Expired CA1120747A (fr)	1976-05-17	1980-09-16	Herbicides

Country Status (1)

Country	Link
CA (1)	CA1120747A (fr)

1980
- 1980-09-16 CA CA000360330A patent/CA1120747A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1999-03-30	MKEX	Expiry

Publication	Publication Date	Title
US4168963A (en)	1979-09-25	Herbicidal agents
US4314069A (en)	1982-02-02	Herbicidal compound, herbicidal composition containing the same, and method of use thereof
US4339443A (en)	1982-07-13	Compounds and compositions
US4315765A (en)	1982-02-16	Trialkylsulfonium salts of n-phosphonomethylglycine and their use as plant growth regulators and herbicides
US4370489A (en)	1983-01-25	Herbicidal compounds
US4421548A (en)	1983-12-20	Herbicidally active 2-substituted 5-penoxyphenylphosphonic acid derivatives
JPS5840947B2 (ja)	1983-09-08	トリフルオロメチルピリドキシフェノキシプロピオン酸誘導体
US4341549A (en)	1982-07-27	Phosphonium salts of N-phosphonomethylglycine and their use as herbicides and plant growth regulants
CA1120747A (fr)	1982-03-30	Herbicides
CA1088065A (fr)	1980-10-21	Agents insecticides
US3032406A (en)	1962-05-01	Herbicidal method employing phenoxyalkylamines
US3305348A (en)	1967-02-21	Herbicidal composition and method employing diamino-s-triazine derivatives
US4376644A (en)	1983-03-15	Tri-mixed alkylsulfonium salts of N-phosphonomethylglycine and their use as plant growth regulators and herbicides
US2875123A (en)	1959-02-24	Hexachlorobicycloheptene sulfonic acids and derivatives as insecticides
NZ205526A (en)	1987-04-30	Phosphorus-containing derivatives of acetic acid as herbicides and plant growth regulants
US4421547A (en)	1983-12-20	4-Hydroxy-5-isopropyl-2-methylphenyl trimethylammonium, 1-piperidine carboxylate salt of N-phosphonomethylglycine and its use as a herbicide
US4434108A (en)	1984-02-28	Herbicidally active 2-nitro-5-(2'-chloro-4'-trifluoromethylphenoxy)phenylphosphinic acid derivatives
US4084953A (en)	1978-04-18	N-hydroxy-N-phosphonomethylglycines and the herbicidal use thereof
US4132542A (en)	1979-01-02	Organic(thio) phosphoric acid ester compounds and herbicidal compositions
CS210604B2 (en)	1982-01-29	Herbicide and preparation method of active substance
JPS6030301B2 (ja)	1985-07-16	シクロプロパンカルボン酸３−（２，２−ジクロロビニルオキシ）ベンジルエステル、その製造方法及び該化合物を含有する殺虫、殺ダニ剤
HU185007B (en)	1984-11-28	Herbicide composition and process for preparing the active substances, n-trifluoro-acetyl-n-phospono-methyl-glycine esters
US4104401A (en)	1978-08-01	Control of insects and acarids with alkynyl phenylphenol divalent aliphatic sulfites
EP0433446B1 (fr)	1992-12-30	Composes herbicides a base d'organophosphore
CS246087B2 (en)	1986-10-16	Herbicide and method of efficient substances production